Name: 38222-83-2|2,6-Di-Tert-butyl-4-methylpyridine|98%
Brand: Ambeed
SKU: A105364
Price: 8.0 USD
Availability: InStock
Rating: 93 (26 reviews)

1
[ 421-20-5 ]
[ 38222-83-2 ]
[ 78020-53-8 ]

Reference： [1]Chemische Berichte,1981,vol. 114,p. 1455 - 1463

2
[ 421-20-5 ]
[ 38222-83-2 ]
2,6-di-tert-butyl-4-methylpyridinium fluorosulfate [ No CAS ]
[ 78008-53-4 ]

Reference： [1]Journal of Organic Chemistry,1982,vol. 47,p. 1977 - 1979
[2]Journal of Organic Chemistry,1982,vol. 47,p. 1977 - 1979

3
[ 421-20-5 ]
[ 38222-83-2 ]
[ 78008-53-4 ]

Reference： [1]Chemische Berichte,1981,vol. 114,p. 1455 - 1463

4
[ 421-20-5 ]
[ 38222-83-2 ]
2,6-Bis(1,1-dimethylethyl)-1,4-dimethylpyridiniumperchlorat [ No CAS ]

Reference： [1]Chemische Berichte,1981,vol. 114,p. 1455 - 1463

5
[ 38222-83-2 ]
[ 612-12-4 ]
[ 118066-99-2 ]

Reference： [1]Synthetic Communications,1988,vol. 18,p. 1449 - 1452

6
[ 38222-83-2 ]
[ 2926-30-9 ]
[ 135182-72-8 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1991,vol. 64,p. 1081 - 1092

7
[ 38222-83-2 ]
[ 107-30-2 ]
[ 107082-94-0 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 1623 - 1624

8
[ 38222-83-2 ]
[ 81142-31-6 ]

Reference： [1]Synthetic Communications,1988,vol. 18,p. 1449 - 1452
[2]Journal of Organic Chemistry,1982,vol. 47,p. 1977 - 1979

9
[ 630-18-2 ]
[ 41792-83-0 ]
[ 38222-83-2 ]

Reference： [1]Journal of Organic Chemistry,1980,vol. 45,p. 168 - 169

10
[ 75-85-4 ]
[ 1538-75-6 ]
[ 38222-83-2 ]
[ 108154-12-7 ]
[ 108154-13-8 ]

Reference： [1]Bulletin de la Societe Chimique de France,1986,p. 307 - 313
[2]Bulletin de la Societe Chimique de France,1986,p. 307 - 313

11
[ 38222-83-2 ]
[ 615-43-0 ]
[ 143321-89-5 ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoroacetic anhydride; In dichloromethane; water;	Example 6B 2,2,2-Trifluoro-N-(2-iodophenyl)acetamide 2-Iodo-phenylamine (Aldrich, 1.09 g, 5 mmol) was treated with trifluoroacetic anhydride (Aldrich, 1.26 g, 6 mmol) and 2,6-di-tert-butyl-4-methyl-pyridine (Aldrich, 1.23 g, 6 mmol) in CH2Cl2 (10 mL)at room temperature overnight. It was then quenched with with water (5 mL) and extracted with EtOAc (3*10 mL). The extracts were combined and washed with brine (5 mL). The organic solution was concentrated and the title compound was purified by flash chromatography (SiO2, Hexanes/EtOAc, 80:20, Rf. 0.50) as a solid (1.1 g, yield, 70percent). 1H NMR (300 MHz, CD3OD) delta 7.07-7.12 (m, 1H), 7.39-7.47 (m, 2H), 7.95 (dd, J=7.8, 1.3 Hz, 1H) ppm. MS (DCI): m/z 316 (M+H)+.

Reference： [1]Patent: US2005/245531,2005,A1

12
[ 38222-83-2 ]
[ 358-23-6 ]
[ 1879-06-7 ]
1-methyl-4-[1-(trifluoromethylsulphonyloxy)vinyl]-1-cyclohexene [ No CAS ]

Reference： [1]Biochemical Pharmacology,1999,vol. 57,p. 801 - 809

13
[ 38222-83-2 ]
2,6-di-tert-4-(fluoromethyl)pyridine [ No CAS ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2006,vol. 181,p. 405 - 412

14
[ 38222-83-2 ]
[ 862009-38-9 ]

Reference： [1]Synthesis,2005,p. 1383 - 1388

15
[ 38222-83-2 ]
[ 862009-40-3 ]

Reference： [1]Synthesis,2005,p. 1383 - 1388

16
[ 38222-83-2 ]
[ 862009-39-0 ]

Reference： [1]Synthesis,2005,p. 1383 - 1388

17
[ 38222-83-2 ]
4,4'-bis[3,5-bis(2,6-di-tert-butylpyridin-4-ylmethoxy)benzyloxy]biphenyl [ No CAS ]

Reference： [1]Synthesis,2005,p. 1383 - 1388

18
[ 38222-83-2 ]
[ 81869-04-7 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 1623 - 1624

19
[ 38222-83-2 ]
C₂₈H₄₄N₂*2FHO₃S [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1982,vol. 47,p. 1977 - 1979

20
[ 38222-83-2 ]
[ 81142-34-9 ]

Reference： [1]Journal of Organic Chemistry,1982,vol. 47,p. 1977 - 1979

21
[ 3282-30-2 ]
[ 38222-83-2 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1959,vol. 625,p. 74,83

22
[ 38222-83-2 ]
[ 17159-79-4 ]
[ 122948-57-6 ]

Yield	Reaction Conditions	Operation in experiment
	With trifluorormethanesulfonic acid; In dichloromethane; at 25℃;	(1) To a solution of 4-oxocyclohexanecarboxylic acid ethyl ester (8.0 g) and 2,6-di(tert-butyl)-4-methylpyridine (14.4 g) in dichloromethane (200 ml) is added trifluoromethanesulfonic anhydride (8.73 ml) at -78°C, and the mixture is gradually warmed to 25°C, and the mixture is stirred at the same temperature overnight.. The reaction solution is poured into aqueous sodium hydrogen carbonate solution, and the mixture is extracted with ethyl acetate.. The organic layer is washed with saturated brine, and the solvent is evaporated under reduced pressure to give 4-trifluoromethanesulfonyloxy-3-cyclohexenecarboxylic acid ethyl ester.

Reference： [1]Patent: EP1371646,2003,A1 .Location in patent: Page 40

23
[ 38222-83-2 ]
[ 53123-88-9 ]
[ 1111-92-8 ]
[ 3283-12-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; In dichloromethane; ethyl acetate;	Dimethyl-phosphinic acid C-43 rapamycin ester To a cooled (0° C.) solution of rapamycin (0.1 g, 0.109 mmol) in 1.8 mL of dichloromethane was added 0.168 g (0.82 mmol) of 2,6-di-t-butyl-4-methyl pyridine, under a stream of N2, followed immediately by a solution of dimethylphosphinic chloride (0.062 g, 0.547 mmol) in 0.2 mL of dichloromethane. The slightly yellow reaction solution was stirred at 0° C., under an atmosphere of N2, for 3.5 h (reaction monitored by TLC). The cold (0° C.) reaction solution was diluted with ~20 mL EtOAc then transferred to a separatory funnel containing EtOAc (150 mL) and saturated NaHCO3 (100 mL). Upon removing the aqueous layer, the organic layer was washed successively with ice cold 1N HCl (1100 mL), saturated NaHCO3(1100 mL), and brine (1*100 mL), then dried over MgSO4 and concentrated. The crude product was purified by silica gel flash chromatography (eluted with 1:10:3:3 MeOH/DCM/EtOAc/hexane) to provide 0.092 g of a white solid: 1H NMR (300 MHz, CDCl3) d 4.18 (m, 1H), 4.10 (m, 1H), 3.05 (m, 1H), 1.5 (m, 6H); 31P NMR (121 MHz, CDCl3) d 53.6; 1013 m/z (M+Na).
	With sodium hydrogencarbonate; In dichloromethane; ethyl acetate;	Dimethyl-phosphinic acid C-43 rapamycin ester To a cooled (0° C.) solution of rapamycin (0.1 g, 0.109 mmol) in 1.8 mL of dichloromethane was added 0.168 g (0.82 mmol) of 2,6-di-t-butyl-4-methyl pyridine, under a stream of N2, followed immediately by a solution of dimethylphosphinic chloride (0.062 g, 0.547 mmol) in 0.2 mL of dichloromethane. The slightly yellow reaction solution was stirred at 0° C., under an atmosphere of N2, for 3.5 h (reaction monitored by TLC). The cold (0° C.) reaction solution was diluted with ~20 mL EtOAc then transferred to a separatory funnel containing EtOAc (150 mL) and saturated NaHCO3 (100 mL). Upon removing the aqueous layer, the organic layer was washed successively with ice cold 1N HCl (1100 mL), saturated NaHCO3(1100 mL), and brine (1*100 mL), then dried over MgSO4 and concentrated. The crude product was purified by silica gel flash chromatography (eluted with 1:10:3:3 MeOH/DCM/EtOAc/hexane) to provide 0.092 g of a white solid: 1H NMR (300 MHz, CDCl3) d 4.18 (m, 1H), 4.10 (m, 1H), 3.05 (m, 1H), 1.51 (m, 6H); 31P NMR (121 MHz, CDCl3) d 53.6; 1013 m/z (M+Na).
	With sodium hydrogencarbonate; In dichloromethane; ethyl acetate;	EXAMPLE 2Dimethyl-Phosphinic Acid C-43 Rapamycin EsterTo a cooled (0° C.) solution of rapamycin (0.1 g, 0.109 mmol) in 1.8 mL of dichloromethane was added 0.168 g (0.82 mmol) of 2,6-di-t-butyl-4-methyl pyridine, under a stream of N2, followed immediately by a solution of dimethylphosphinic chloride (0.062 g, 0.547 mmol) in 0.2 mL of dichloromethane.The slightly yellow reaction solution was stirred at 0° C., under an atmosphere of N2, for 3.5 h (reaction monitored by TLC).The cold (0° C.) reaction solution was diluted with ~20 mL EtOAc then transferred to a reparatory funnel containing EtOAc (150 mL) and saturated NaHCO3 (100 mL).Upon removing the aqueous layer, the organic layer was washed successively with ice cold 1N HCl (1100 mL), saturated NaHCO3(1100 mL), and brine (1*100 mL), then dried over MgSO4 and concentrated.The crude product was purified by silica gel flash chromatography (eluted with 1:10:3:3 MeOH/DCM/EtOAc/hexane) to provide 0.092 g of a white solid: 1H NMR (300 MHz, CDCl3) delta4.18 (m, 1H), 4.10 (m, 1H), 3.05 (m, 1H), 1.51 (m, 6H); 31P NMR (121 MHz, CDCl3) delta 53.6; 1013 m/z (M+Na).

Reference： [1]Patent: US2003/220297,2003,A1
[2]Patent: US2005/32825,2005,A1
[3]Patent: US2012/289481,2012,A1

24
[ 38222-83-2 ]
[ 503464-97-9 ]
[ 1025373-45-8 ]
[ 503464-98-0 ]

Yield	Reaction Conditions	Operation in experiment
75%	In dichloromethane;	EXAMPLE 3 Synthesis of Trifluoromethanesulfonic Acid 2,2-bis(fluoromethyl)-6-(trifluoromethyl)-2H-1-benzopyran-4-yl ester A three-necked 50-ml flask (equipped with a thermometer and a dropping funnel) was charged with 1.0 g (3.6 mmol) of 2,2-bis(fluoromethyl)-3,4-dihydro-6-(trifluoromethyl)-2H-1-benzopyran-4-one, 1.8 g (8.9 mmol) of <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong>, and 10 ml of methylene chloride. Then, 2.0 g (7.1 mmol) of trifluoromethanesulfonic acid anhydride were added in a dropwise manner by spending 5 minutes to the mixture under cooling in an iced water bath at 5-10° C., while the mixture was stirred. After completing the dropping, the temperature of the mixture was gradually increased to room temperature, followed by stirring for 140 hr at room temperature. Then, the methylene chloride was distilled off by an evaporator. The resulting residue was purified by silica gel column chromatography (developing liquid: ethyl acetate/n-hexane=1/8), thereby obtaining 1.1 g (2.7 mmol) of trifluoromethanesulfonic acid 2,2-bis(fluoromethyl)-6-(trifluoromethyl)-2H-1-benzopyran-4-yl ester (yield: 75percent). This product was found to have the following properties. 1H-NMR (standard substance: TMS; solvent: CDCl3) sigma (ppm): 4.51-4.73 (m, J=46.4 Hz, 4H), 5.78 (s, 1H), 7.04 (d, J=8.8 Hz, 1H), 7.53 (d, J=2.0 Hz, 1H), 7.58 (dd, J=8.8, 2.0 Hz, 1H) 19F-NMR (standard substance: CCl3F; solvent: CDCl3) sigma (ppm): -62.85 (s, 3F), -73.51 (s, 3F), -232.91 (t, J=46.4 Hz, 2F)

Reference： [1]Patent: US2003/109574,2003,A1

25
[ 38222-83-2 ]
[ 374753-43-2 ]
[ 1493-13-6 ]
[ 374753-44-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium hydrogencarbonate; In dichloromethane; water;	EXAMPLE 7 Preparation of 4-[6-(4-methoxyphenyl)benzo[b]thiophen-3-yl]pyridine Anhydrous trifluoromethane sulfonic acid (Tf2O; 0.14 ml, 0.8322 mmol) was added to a suspension of 3-(4-pyridyl)benzo[b] thiophen-6-ol (164 mg, 0.7216 mmol) obtained in Example 6 and 2,6-di-t-butyl-4-methylpyridine (180 mg, 0.8766 mmol) in dichloromethane (5 ml) under cooling with ice. The mixture was warmed to room temperature and stirred for 2 hours. The reaction mixture was concentrated under reduced pressure. The resulting residue was diluted with ethyl acetate. The organic layer was washed with 5percent citric acid aqueous solution, saturated aqueous solution of sodium bicarbonate, water, and then saturated brine, sequentially, and dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue obtained was submitted to silica gel column chromatography (hexane:ethyl acetate=17:3) to obtain a colorless oily product of 3-(4-pyridyl)benzo[b]thiophen-6-yl=trifluoromethane sulfonate (247 mg, 95percent). 1H-NMR(CDCl3) delta: 7.33(dd, J=2.4, 8.9 Hz, 1H), 7.46(d, J=6.0 Hz, 2H), 7.65(s, 1H), 7.85(d, J=2.2 Hz, 1H), 7.93(d, J=8.9 Hz, 1H), 8.73(d, J=6.0 Hz, 2H).

Reference： [1]Patent: US2003/130340,2003,A1

26
[ 491-37-2 ]
[ 38222-83-2 ]
[ 461666-59-1 ]

Yield	Reaction Conditions	Operation in experiment
94%	With trifluoromethanesulfonic acid anhydride; In hexane; dichloromethane;	(34a) Trifluoromethanesulfonic anhydride (1.2 mL, 7.4 mmol)was added drop wise to a stirring solution of chroman-4-one (1.0 g, 6.7 mmol), 2,6-di-t-butyl-4-methyl pyridine (1.59 g, 7.7 mmol) in dichloromethane (40 mL), under nitrogen atmosphere. The reaction was heated to reflux for 2 h, allowed to cool to room temperature and was concentrated in vacuo to give a semi solid residue. This was treated with hexane and the solids were filtered off. The filtrate was concentrated to give 4-[(trifluoromethyl)sulfonyl]-2H-chromene (1.78 g, 94percent) as an orange oil.

Reference： [1]Patent: US2003/87882,2003,A1

27
[ 38222-83-2 ]
[ 374753-45-4 ]
[ 374753-52-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	With Tf2O; sodium hydrogencarbonate; In dichloromethane; water;	EXAMPLE 13 Preparation of 3-[6-(4-fluorophenyl)benzo[b]thiophen-3-yl]pyridine hydrochloride Tf2O (0.97 ml, 5.766 mmol) was added to a suspension of the 3-(3-pyridyl)benzo[b]thiophen-6-ol (1.14 g, 5.016 mmol) obtained in Example 8 and 2,6-di-t-butyl-4-methylpyridine (1.25 g, 6.087 mmol) in dichloromethane (35 ml) under cooling with ice. The mixture was warmed to room temperature and stirred for 2.5 hours. The reaction mixture was concentrated under reduced pressure. The resulting residue was diluted with diethyl ether, washed with water, 5percent citric acid aqueous solution, saturated aqueous solution of sodium bicarbonate, water, and then saturated brine, sequentially, and dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The resulting residue was submitted to basic silica gel column chromatography (hexane:ethyl acetate=93:7) to obtain a colorless oily product of 3-(3-pyridyl)benzo[b]thiophen-6-yl=trifluoromethane sulfonate (1.78 g, 99percent). 1H-NMR(CDCl3) delta: 7.32(dd, J=2.3, 8,9 Hz, 1H), 7.42(dd, J=4.9, 7.9 Hz, 1H), 7.57(s, 1H), 7.84-7.86(m, 3H), 8.67(dd, J=2.1, 5.5 Hz, 1H), 8.80(d, J=2.1 Hz, 1H).

Reference： [1]Patent: US2003/130340,2003,A1

28
[ 3528-17-4 ]
[ 38222-83-2 ]
[ 461665-48-5 ]

Yield	Reaction Conditions	Operation in experiment
51%	With trifluoromethanesulfonic acid anhydride; In hexane; dichloromethane;	(33a) Trifluoromethanesulfonic anhydride (2.2 mL, 13.4 mmol) was added dropwise to a stirring solution of thiochroman-4-one (2.0 g, 12.2 mmol), 2,6-di-t-butyl-4-methyl pyridine (2.63 g, 12.8 mmol) in dichloromethane (100 mL), under nitrogen atmosphere. The reaction was heated to reflux for 2 h, allowed to cool to room temperature and was concentrated in vacuo to give a semi-solid residue. This was treated with hexane and the solids were filtered off. The filtrate was concentrated to give 2H-1-benzothiopyran-4-yltrifluoromethyl sulfone (1.84 g, 51percent) as a solid. MS found: (M+H)+=297.

Reference： [1]Patent: US2003/87882,2003,A1

29
[ 38222-83-2 ]
[ 358-23-6 ]
[ 267875-65-0 ]
[ 267875-66-1 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; pentane;	Step H 2,2-Difluoro-2-(2-pyridyl)ethyl trifluoromethanesulfonate (1-8) To a stirred -78° C. solution of 50 mg (0.31 mmol) of 2,2-difluoro-2-(2-pyridyl)ethanol and 100 mg (0.49 mmol) of 2,6-di-t-butyl-4-methylpyridine in 1.0 ml of CH2Cl2 was added dropwise 79 muL (0.47 mmol) of trifluoromethansulfonic anhydride. After the addition, the cold bath was removed, and stirring continued for 0.5 h. The reaction was diluted with 2 ml of pentane, and the resulting precipitate washed with pentane. The filtrate was evaporated in vacuo to dryness to give as a yellow solid: 1H NMR (CDCl3) delta8.66 (d, 1H, 4.9 Hz), 7.89 (td,1H, 7.7, 1.7 Hz), 7.76 (d, 1H, 7.9 Hz), 7.45-7.49 (m, 1H), 5.12 (t, 2 H, 11.9 Hz).
	In dichloromethane; pentane;	Step B 2,2-Difluoro-2-(2-pyridyl)ethyl Trifluoromethanesulfonate To a stirred -78° solution of 50 mg (0.31 mmol) of 2,2-difluoro-2-(2-pyridyl)ethanol and 100 mg (0.49 mmol) of 2,6-di-t-butyl-4-methylpyridine in 1.0 mL of CH2Cl2 was added 79 muL (0.47 mmol) of trifluoromethansulfonic anhydride dropwise under Ar. After the addition, the cold bath was removed, and stirring continued for 0.5 h. The reaction was diluted with 2 mL of pentane, and the resulting precipitate washed with pentane. The filtrate was evaporated in vacuo to dryness to give the title compound as a yellow solid: 1H NMR (CDCl3) delta 8.66 (d, 1H, 4.9 Hz), 7.89 (td, 1H, 7.7, 1.7 Hz), 7.76 (d, 1H, 7.9 Hz), 7.45-7.49 (m, 1H), 5.12 (t, 2; H, 11.9 Hz).

Reference： [1]Patent: US2002/35115,2002,A1
[2]Patent: US6610692,2003,B1

30
[ 38222-83-2 ]
[ 40353-34-2 ]
[ 358-23-6 ]
trifluoromethanesulphonic acid 7-nitro-3,4,4a,8a-tetrahydronaphthalen-1-yl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; pentane;	Step 1 Trifluoromethanesulphonic acid 7-nitro-3,4,4a,8a-tetrahydronaphthalen-1-yl ester 9.8 ml of trifluoromethanesulphonic anhydride are poured at 0° C. into a solution of 10 g of 7-nitrotetralone and 11.8 g of <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> in 365 ml of dichloromethane. After 24 hours at ambient temperature, concentration to dryness and taking up the residue in 200 ml of pentane at reflux for 30 minutes, the precipitate formed is filtered off. The organic phase is washed with a 1N hydrochloric acid solution and then with water, dried over magnesium sulphate and concentrated.

Reference： [1]Patent: US2002/25965,2002,A1

31
[ 38222-83-2 ]
[ 267875-65-0 ]
[ 267875-66-1 ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoromethylsulfonic anhydride; In dichloromethane; pentane;	2,2-Difluoro-2-(2-pyridyl)ethyl trifluoromethanesulfonate (I-1-4) To a stirred solution of 5 g (31.4 mmol) of 2,2-difluoro-2-(2-pyridyl)ethanol I-1-3 and 9.69 g (47.2 mmol) of 2,6-di-t-butyl-4-methylpyridine in 110 mL of methylene chloride at -78° C. under Ar was added 7.93 mL (47.2 mmol) of triflic anhydride dropwise. After 1 h, the reaction was diluted with 100 mL of pentane and filtered. The filtrate was concentrated and treated again with pentane and filtered. Concentration of the filtrate gave I-1-4 as a brown oil, contaminated with 2,6-di-t-butyl-4-methylpyridine: 1H NMR (CDCl3) delta5.12 (t, 2H), 7.45-7.5 (m, 1H), 7.75 (d,1H), 7.86-7.94 (m, 1H), 8.65 (d, 1H).
	With trifluoromethylsulfonic anhydride; In dichloromethane; pentane;	Step E 2,2-Difluoro-2-(2-pyridyl)ethyl trifluoromethanesulfonate (5a) To a stirred solution of 5 g (31.4 mmol) of 2,2-difluoro-2-(2-pyridyl)ethanol 5 and 9.69 g (47.2 mmol) of 2,6-di-t-butyl-4-methylpyridine in 110 mL of methylene chloride at -78° C. under Ar was added 7.93 mL (47.2 mmol) of triflic anhydride dropwise. After 1 h, the reaction was diluted with 100 mL of pentane and filtered. The filtrate was concentrated and treated again with pentane and filtered. Concentration of the filtrate gave 5a as a brown oil, contaminated with 2,6-di-t-butyl-4-methylpyridine: 1H NMR (CDCl3) delta5.12 (t, 2H), 7.45-7.5 (m, 1H), 7.75 (d, 1H), 7.86-7.94 (m, 1H), 8.65 (d, 1H).
	With trifluoromethylsulfonic anhydride; In dichloromethane; pentane;	2,2-Difluoro-2-(2-pyridyl)ethyl Trifluoromethanesulfonate (1-4). To a stirred solution of 5 g (31.4 mmol) of 2,2-difluoro-2-(2-pyridyl)ethanol 1-3 and 9.69 g (47.2 mmol) of 2,6-di-t-butyl-4-methylpyridine in 110 mL of methylene chloride at -78° C. under Ar was added 7.93 mL (47.2 mmol) of triflic anhydride dropwise. After 1 h, the reaction was diluted with 100 mL of pentane and filtered. The filtrate was concentrated and treated again with pentane and filtered. Concentration of the filtrate gave 1-4 as a brown oil, contaminated with 2,6-di-t-butyl-4-methylpyridine: 1H NMR (CDCl3) delta 5.12 (t, 2H), 7.45-7.5 (m, 1H), 7.75 (d, 1H), 7.86-7.94 (m, 1H), 8.65 (d, 1H).

Reference： [1]Patent: US2002/193398,2002,A1
[2]Patent: US6387911,2002,B1
[3]Patent: US6455532,2002,B1

32
[ 38222-83-2 ]
[ 247568-68-9 ]
[ 420-37-1 ]
[ 247567-42-6 ]

Yield	Reaction Conditions	Operation in experiment
	In 1,2-dichloro-ethane;	EXAMPLE 64(3) To a solution of (R)-N-(3,4-dimethoxybenzyl)-2-(2-hydroxy-1-methylethylamino)-5-nitrobenzamide (200 mg) in 1,2-dichloroethane (10 mL) were added trimethyloxonium tetrafluoroborate (91.2 mg) and <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (158 mg), and the mixture was heated for 3 hours under reflux. The mixture was washed with 1N-hydrochloric acid, water, an aqueous saturated sodium bicarbonate solution and brine. Then, the resultant was dried over magnesium sulfate and evaporated in vacuo. The residue was purified by a silica gel column chromatography eluding with a mixture of hexane and ethyl acetate (3:1 to 1:1). The obtained product was triturated with diisopropyl ether to give (R)-N-(3,4-dimethoxybenzyl)-2-(2-methoxy-1-methylethylamino)-5-nitrobenzamide as yellow powders (145 mg). NMR (DMSO-d6, delta): 1.17 (3H, d, J=7 Hz), 3.29 (3H, s), 3.42 (2H, br), 3.73 (3H, s), 3.74 (3H, s), 3.88-4.00 (1H, br), 4.37 (2H, d, J=7 Hz), 6.85-6.96 (4H, m), 8.12 (1H, dd, J=4, 8 Hz), 8.59 (1H, d, J=4 Hz), 9.09 (1H, d, J=8 Hz), 9.29 (1H, br); Mass m/z: 402(M+).

Reference： [1]Patent: US6384080,2002,B1

33
[ 38222-83-2 ]
4'-5' dibromomethylfluorescein di-t-butyldiphenylsilyl ether [ No CAS ]
4',5'-Dinitrooxymethylfluorescein Di-t-butyldiphenylsilyl Ether [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With silver nitrate; In 1,4-dioxane; water;	l) 4',5'-Dinitrooxymethylfluorescein Di-t-butyldiphenylsilyl Ether (Formula 28) Silver nitrate (20 mg, 0.12 mmol) was dissolved in a minimal portion of water (~1 mL) and added to a stirring solution of 4',5'-dibromomethylfluorescein di-t-butyldiphenylsilyl ether (Formula 27) (25 mg, 25 mumol) and 2,6-di-t-butyl-4-methylpyridine (10 mg, 49 mumol) in 5 mL of dioxane. The reaction mixture was stirred for 12 h at room temperature. The gray silver precipitate was removed by filtration and the solvents were removed. Flash chromatography (7:3 hexanes/EtOAc) yielded the product as a white solid (15 mg, 62percent). TLC Rf=0.56 (7:3 hexanes/EtOAc). 1H NMR (CDCl3) delta 111(18H, s), 6.06 (4H, s), 6.16 (2H, d, J=9.0 Hz), 6.35 (2H, d, J=9.0 Hz), 7.13 (1H, d, J=7.5 Hz), 7.33-7.60 (14H, m), 7.65-7.70 (8H, m), 7.85 (1H, d, J=7.5 Hz). FTIR (KBr, cm-1) 2957, 2931, 2859, 1764, 1633, 1607, 1575, 1491, 1472, 1428, 1392, 1363, 1276, 1228, 1109, 971, 942, 910, 858, 837, 823, 745, 701, 615, 546, 501, 440, 418.

Reference： [1]Patent: US2002/106697,2002,A1

34
[ 38222-83-2 ]
3-benzyloxy-estrone [ No CAS ]
3-Benzyloxy-17-(trifluoromethanesulfonyl)estra-1,3,5⁽¹⁰⁾,16-tetraene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84.5%	With trifluoromethylsulfonic anhydride; In dichloromethane;	Synthesis of 3-Benzyloxy-17-(trifluoromethanesulfonyl)estra-1,3,5(10),16-tetraene (compound 3) To a solution of compound 2, comprising 4.8 g (13 mmol) of compound 2 in CH2Cl2 (70 ml) was added <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (3 g, 14 mmol) and triflic anhydride (6 g, 27 mmol) at 0° C. The mixture was stirred for 5 hrs at room temperature and the mixture was filtered and the filtrate was washed with 10percent sodium bicarbonate solution. The solution was then dried (Na2SO4), filtered and evaporated and chromatographed (petroleum ether:ethyl acetate, 2:1) to give a yellowish solid (5.2 g, 84.5percent) (compound 3).

Reference： [1]Patent: US6376687,2002,B1

35
[ 202648-54-2 ]
[ 38222-83-2 ]
[ 420-37-1 ]
[ 202648-55-3 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane;	PREPARATION 108 Methyl 2-O-Benzyl-3-O-p-methoxybenzyl-6-O-methyl-alpha-D-glucopyranoside (122) Compound 121 (26.4 g) is dissolved in dichloromethane (263 ml) under a nitrogen atmosphere. Trimethyloxonium tetrafluoroborate (11.6 g) and <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (17.4 g) are added at room temperature. After 4 hours, the mixture is poured onto ice-water and extracted with dichloromethane. The organic phase is washed with sodium hydrogen carbonate and concentrated. Purification of the crude product by chromatography on a column of silica gel allows 18.5 g of compound 122 to be obtained. TLC: Rf=0.25, silica gel, 7/3 v/v toluene/ethyl acetate

Reference： [1]Patent: US6534481,2003,B1

36
[ 38222-83-2 ]
[ 267875-74-1 ]
[ 267875-75-2 ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoromethanesulfonic acid anhydride; In dichloromethane; pentane;	Step C 3-Cyclopropyl-2,2-difluoropropyl trifluoromethanesulfonate To a 0° C. solution of 952 mg (7.0 mmol) of 3-cyclopropyl-2,2-difluoropropanol and 5.0 g (18 mmol) of 2,6-di-t-butyl-4-methylpyridine in 7 mL of CH2Cl2 was added 5.0 g of trifluoromethanesulfonic anhydride dropwise under Ar. The cold bath was removed and the mixture stirred overnight. The reaction mixture was diluted with 100 mL of pentane, and the precipitate removed by filtration. The filter cake was washed with pentane, and the filtrate washed with two portions of cold 1M HCl, brine, dried over Na2SO4 and the solvents removed at reduced pressure to give the title compound as an oil: 1H NMR (CDCl3) delta 4.62 (t, 2H, 11.4 Hz), 1.91 (td, 2H, 15.6, 7.1 Hz), 0.79-0.88 (m, 1H), 0.58-0.63 (m, 2H), 0.17-0.23 (m, 2H).

Reference： [1]Patent: US6610692,2003,B1

37
[ 38222-83-2 ]
[ 217978-01-3 ]
[ 345963-90-8 ]

Yield	Reaction Conditions	Operation in experiment
85%	With trifluoromethanesulfonic acid anhydride; In hexane; dichloromethane;	Ethyl-2-fluoro-4-trifluoromethylsulfonyloxy-benzoate (Intermediate 6) A stirred, cooled (ice bath) solution of ethyl-2-fluoro-4-hydroxy-benzoate (Intermediate 5, 0.368 g, 2 mmol) and 2,6-di-tert-butyl-4-methyl-pyridine (0.81 g, 8 mmol) in 8 mL of dichloromethane was treated with trifluoromethanesulfonic anhydride (0.1 g, 4 mmol). The reaction mixture was allowed to warm to ambient temperature and stirred overnight. The reaction mixture was subjected to flash column chromatography over silica gel (230-400 mesh) using 5-10percent ethyl acetate in hexane as the eluent to afford the title compound (0.53 g, 85percent). 1H-NMR (300 MHz, CDCl3): delta1.41 (t, J=7.3 Hz, 3H), 4.42 (q, J=7.1 Hz, 2H), 7.12-7.20(m, 2H), 8.08(t, J=8.3 Hz, 1H).
85%	With trifluoromethanesulfonic acid anhydride; In hexane; dichloromethane;	Ethyl-2-fluoro-4-trifluoromethylsulfonyloxy-benzoate (Intermediate 6) A stirred, cooled (ice bath) solution of ethyl-2-fluoro-4-hydroxy-benzoate (Intermediate 5, 0.368 g, 2 mmol) and 2,6-di-tertbutyl-4-methyl-pyridine (0.81 g, 8 mmol) in 8 mL of dichloromethane was treated with trifluoromethanesulfonic anhydride (0.1 g, 4 mmol). The reaction mixture was allowed to warm to ambient temperature and stirred overnight. The reaction mixture was subjected to flash column chromatography over silica gel (230-400 mesh) using 5-10percent ethyl acetate in hexane as the eluent to afford the title compound (0.53 g, 85percent). 1H-NMR (300 MHz, CDCl3): delta 1.41 (t, J=7.3 Hz, 3H), 4.42 (q, J=7.1 Hz, 2H), 7.12-7.20(m, 2H), 8.08(t, J=8.3 Hz, 1H).

Reference： [1]Patent: US6313107,2001,B1
[2]Patent: US6252090,2001,B1

38
[ 38222-83-2 ]
N-(3,5-dichloropyrid-4-yl)-3-cyclopentyloxy-4-(methylthio)-benzamide [ No CAS ]
N-(3,5-dichloropyrid-4-yl)-3-cyclopentyloxy-4-(fluoromethylthio)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In molecular sieve; xenon difluoride; dichloromethane;	EXAMPLE 28 Compound C A solution of N-(3,5-dichloropyrid-4-yl)-3-cyclopentyloxy-4-(methylthio)benzamide (1 g; that is prepared as described in Example 20) in dichloromethane (100 mL), containing molecular sieve 4A, under nitrogen, is treated with <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (1.28 g). The resulting mixture is stirred at room temperature for 1.5 hours, and then it is cooled to 0° C. (in an ice/salt bath) and treated with xenon difluoride (0.51 g) in one portion. After stirring for a further 2 hours in the cold, the mixture is filtered, and the filtrate is washed with saturated aqueous ammonium chloride solution. The organic phase is dried over sodium sulfate and evaporated. The resulting residue is subjected to flash chromatography, eluding with a mixture of ethyl acetate and pentane (2:3 v/v), to give impure N-(3,5-dichloropyrid-4-yl)-3-cyclopentyloxy-4-(fluoromethylthio)-benzamide (600 mg). It is further purified by reversed phase HPLC on octadecylsilyl silica gel, eluding with a mixture of methanol and water (7:3 v/v), to give N-(3,5-dichloropyrid-4-yl)-3-cyclopentyloxy-4-(fluoromethylthio)benzamide (519 mg), in the form of a white solid, m.p. 111-113° C. Elemental analysis: C,51.50; H,4.12; N,6.74percent; calculated: C,52.05; H,4.12;[N,6.74percent].
	In molecular sieve; xenon difluoride; dichloromethane;	EXAMPLE 28 Compound CI A solution of N-(3,5-dichloropyrid-4-yl)-3-cyclopentyloxy-4-(methylthio)benzamide (1 g; that is prepared as described in Example 20) in dichloromethane (100 mL), containing molecular sieve 4A, under nitrogen, is treated with <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (1.28 g). The resulting mixture is stirred at room temperature for 1.5 hours, and then it is cooled to 0° C. (in an ice/salt bath) and treated with xenon difluoride (0.51 g) in one portion. After stirring for a further 2 hours in the cold, the mixture is filtered, and the filtrate is washed with saturated aqueous ammonium chloride solution. The organic phase is dried over sodium sulfate and evaporated. The resulting residue is subjected to flash chromatography, eluding with a mixture of ethyl acetate and pentane (2:3 v/v), to give impure N-(3,5-dichloropyrid-4-yl)-3-cyclopentyloxy-4-(fluoromethylthio)-benzamide (600 mg). It is further purified by reversed phase HPLC on octadecylsilyl silica gel, eluding with a mixture of methanol and water (7:3 v/v), to give N-(3,5-dichloropyrid-4-yl)-3-cyclopentyloxy-4-(fluoromethylthio)benzamide (519 mg), in the form of a white solid, m.p. 111°-113° C. Elemental analysis: C,51.50; H,4.12; N,6.74percent; calculated: C,52.05; H,4.12;[N,6.74percent].

Reference： [1]Patent: US5935978,1999,A
[2]Patent: US5679696,1997,A

39
[ 38222-83-2 ]
[ 196398-40-0 ]
[ 76-83-5 ]
[ 144-55-8 ]
2-{4-[(3-O-acetyl-4,6-O-benzylidene-1deoxy-2-O-(4-methoxybenzyl)-β-D-galactopyranosyl)thio]phenoxy}acetic acid [ No CAS ]
[ 196398-47-7 ]

Yield	Reaction Conditions	Operation in experiment
171 mg (81%)	With silver trifluoromethanesulfonate; In dichloromethane;	7.30. 2-{4-[(3-O-acetyl-4,6-O-benzylidene-1deoxy-2-O-(4-methoxybenzyl)-beta-D-galactopyranosyl)thio]phenoxy}acetic acid (95) To a solution of 81, prepared as above (139 mg, 0.303 mmol) and 2,6-di-t-butyl-4-methyl pyridine (187 mg, 0.91 mmol) in 5 mL CH2 Cl2, are added chlorotriphenylmethane (101 mg, 0.364 mmol) and silver trifluoromethanesulfonate (78 mg, 0.30 mmol). The reaction mixture is stirred at room temperature for 45 min and then is filtered though celite and washed with 10 mL of aqueous NaHCO3. The aqueous solution is extracted with CH2 Cl2 (2*10 mL) and the organic layers are combined and dried over Na2 SO4, filtered and concentrated. The product is purified by flash chromatography (25percent EtOAc/hexane) to give 171 mg (81percent) of 1-deoxy-3,4-O-isopropylidene-1-{4-[2-(trimethylsilyl)ethoxymethoxy]phenylthio}-6-O-triphenylmethyl-beta-D-galactopyranose 89 as white solid: Rf 0.2 (25percent EtOAc/hexane); 1 H NMR (CDCl3, 300 MHz) delta 7.53-7.40 (m, 8H), 7.31-7.21 (m, 9H), 6.95 (d, J=8.5 Hz, 2H), 5.19 (s, 2H), 4.29 (d, J=10.2 Hz, 1H, H-1), 4.14 (dd, J=5.6, 2.0 Hz, 1H, H-4), 4.02 (dd, J=6.9, 5.6 Hz, 1H, H-3), 3.73 (m, 3H), 3.56 (dd, J=9.6, 6.9 Hz, 1H, H-6), 3.48 (ddd, J=8.9, 6.9, 2.0 Hz, 1H, H-2), 3.36 (dd, J=9.6, 5.3 Hz, 1H, H-6), 2.37 (d, J=2.0 Hz, 1H, OH), 1.37 (s,3H), 1.31 (s, 3H), 0.96 (t, J=7.2 Hz, 2H), 0.00 (s, 9H)

Reference： [1]Patent: US6040433,2000,A

40
[ 38222-83-2 ]
1,2-O-Isopropylidene-3-deoxy-3-azido-D-xylofuranose [ No CAS ]
1,2-O-Isopropylidene-3-deoxy-3-azido-5-trifluoromethanesulfonyloxy-D-xylofuranose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With trifluoromethylsulfonic anhydride; In (CH2 Cl)2; hexane;	1,2-O-Isopropylidene-3-deoxy-3-azido-5-trifluoromethanesulfonyloxy-D-xylofuranose (14). 4-Methyl-2,6-di-t-butylpyridine (1.28 g, 6.3 mmol) was dissolved in 10 mL of dry (CH2 Cl)2 under N2 and then cooled to -78° C. Triflic anhydride (1.05 ml, 6.3 mmol) was added to the solution which was then stirred for 5 minutes. A solution of 13 (1.12 g, 5.2 mmol) in 12 mL of dry (CH2 Cl)2 was added to the triflate solution which was then stirred at -10° C. for 30 minutes. The reaction was warmed to rt, 10 mL of hexane was added, and the solution loaded onto a silica gel column. Elution with 3:7 hexane/CHCl3 afforded triflate 14 (1.41 g, 78percent). FAB HRMS exact mass calcd. for MH+C9 H13 SN3 F3 O6 requires 348.0477, found 348.0477.

Reference： [1]Patent: US6020344,2000,A

41
[ 38222-83-2 ]
[ 108-95-2 ]
7-Bromo-2,3,4,5-tetrahydro-4-(methylsulfonyl)-3-(phenoxymethyl)-1H-1,4-benzodiazepine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30 mg (49%)	With trifluoromethylsulfonic anhydride; In tetrahydrofuran; dichloromethane; mineral oil;	D. 7-Bromo-2,3,4,5-tetrahydro-4-(methylsulfonyl)-3-(phenoxymethyl)-1H-1,4-benzodiazepine To a solution of Compound C (50 mg, 0.15 mmol) in methylene chloride (10 mL) was added <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (62 mg, 0.30 mmol). The solution was cooled to -40° C. under N2. Triflic anhydride (0.85 mL, 0.30 mmol) was added and the solution was stirred under N2 for 1 h at -40° C. In a separate flask, phenol (100 mg, 1.1 mmol) was added to a solution of sodium hydride (44 mg, 1.1 mmol, 60percent dispersion in mineral oil, prewashed with hexanes) in THF (2.5 mL). The solution was stirred for 20 min at ambient temperature under N2 and was added quickly to the triflate solution. After stirring for 20 minutes, the solution was diluted with methylene chloride (40 mL) and washed with saturated aq sodium bicarbonate solution. The organic layer was dried (Na2SO4), filtered and concentrated to give a solid. This material was chromatographed on flash silica eluding with 1:1 ethyl acetate:hexanes to afford 30 mg (49percent) of Compound D as an off-white solid. MS (M+H)+ 411.

Reference： [1]Patent: US6011029,2000,A

42
[ 38222-83-2 ]
[ 204716-63-2 ]
[ 7143-01-3 ]
[ 204716-67-6 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; dichloromethane;	b 3-[1-(3-Methanesulfonyloxymethylbenzyl)-indol-3-yl]-4-(1-methyl-indol-3-yl)-pyrrole-2,5-dione Methanesulfonic anhydride (0.35 g, 2.0 mmol) was added to a stirred solution of the product of step a) (0.234 g, 0.51 mmol) and <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (0.42 g, 2.0 mmol) in dry CH2 Cl2 (15 mL) at room temperature. The reaction mixture was stirred for 16 h, and thereafter quenched by adding methanol (1.5 mL). The solvent was evaporated and the crude product chromatographed (ethyl acetate/heptane: 2/1) to yield 0.285 g of the sub-title product. 1 H-NMR (CDCl3):delta7.76 (1H, s); 7.66 (1H, s); 7.58 (1H, s); 7.38-7.24 (3H, m); 7.22-7.00 (6H, m); 6.82 (1H, d, J=8.05 Hz); 6.77 (1H, t, J=8.30 Hz); 6.68 (1H, t, J=8.05 Hz); 5.34 (2H, s); 5.18 (2H, s); 3.86 (3H, s); 2.83 (3H, s).

Reference： [1]Patent: US6153641,2000,A

43
[ 38222-83-2 ]
trifluoromethane sulfonic anhydride [ No CAS ]
[ 60-29-7 ]
[ 302-97-6 ]
3-(Trifluoromethanesulfonyloxy)-3,5-androstadiene-17β-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; formic acid; In tetrahydrofuran; dichloromethane; water;	Step A (Route 1) A solution of 3-oxo-4-androstene-17beta-carboxylic acid (4.0 g., 12.5 mmoles), 2,6-di-tert-butyl-4-methyl pyridine (8.304 g., 31 mmoles) and trifluoromethane sulfonic anhydride (9.28 g., 33 mmoles) in 40 ml of methylene chloride was stirred at 22° C. for 2 hours and then was kept at 5° C. for 16 hours. The organic solvent was evaporated and the residue was dissolved in 200 ml of tetrahydrofuran containing 1.0 ml of water and 4.5 g. of 4-dimethylaminopyridine. This mixture was stirred at 22° C. for 20 hours and then acidified with 2N hydrochloric acid. The organic solvent was removed and the residue dissolved in methylene chloride, was applied to a column of 400 g. of silica gel. Elution with a 9:1 mixture of CH2 Cl2: ethyl ether, containing 0.4percent of formic acid (88percent) afforded 6.2 g. of pure product. A portion triturated with acetonitrile gave an analytical sample, m.p. 140°-150° C. with decomposition. Calcd.: C, 56.24; H, 6.07. Found: C, 56.71; H, 6.20.

Reference： [1]Patent: US5091380,1992,A

44
[ 38222-83-2 ]
trifluoromethane sulfonic anhydride [ No CAS ]
[ 6650-44-8 ]
17β-benzoyl-3-trifluoromethanesulfonyloxy-3,5-androstadiene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; cyclohexane;	Step A (Route 3) To a solution of 1.3 g. (3.46 mmoles) of the diketosteroid from Example 9 and 9.92 mg. (4.83 mmoles) of <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> in 15 ml. of methylene chloride was added at 0° C., 1.46 g. of trifluoromethane sulfonic anhydride. The reaction at 24° C. colored and darkened, and a precipitate formed. After 30 minutes, the reaction was diluted with methylene chloride and filtered. The filtrate was quickly washed successively with 5N hydrochloric acid, water, saturated sodium bicarbonate solution and saturated sodium chloride solution. The residue obtained on evaporation was chromatographed on 100 g. of silica gel with 9:1 cyclohexane/ethyl acetate to remove a faster moving impurity. Continued elution gave the title compound, 1.21 g., identified by its mass and nmr spectra. This material was used directly in the next Example.

Reference： [1]Patent: US5091380,1992,A

45
[ 38222-83-2 ]
N-(2-adamantyl)-3-oxo-4-androstene-17β-carboxamide [ No CAS ]
trifluoromethane sulfonic anhydride [ No CAS ]
N-(2-Adamantyl)-3-(trifluoromethanesulfonyloxy)-3,5-androstadiene-17β-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; acetone;	Step A (Route 3) A soluton of the adamantyl amide from Example 24 (350 mg., 0.73 mmole), <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (211 mg., 1.03 mmole) and trifluoromethane sulfonic anhydride (416 mg., 1.48 mmole) in 5 ml. of methylene chloride was prepared at 0° C. The mixture warmed to room temperature and was kept at 24° C. for 2.5 hours. Additional methylene chloride was added and the solution was washed successively with dilute hydrochloric acid, dilute sodium bicarbonate solution and water. The residue obtained on concentration was eluted on 3-2000mu silica gel plates with 5percent acetone in methylene chloride. Starting material and the title compound were isolated. The latter, 376 mg., was identified by its nmr and mass spectra.
	In dichloromethane; acetone;	Step A (Route 3) A solution of the adamantyl amide from Example 24 (350 mg., 0.73 mmole), <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (211 mg., 1.03 mmole) and trifluoromethane sulfonic anhydride (416 mg., 1.48 mmole) in 5 ml. of methylene chloride was prepared at 0° C. The mixture warmed to room temperature and was kept at 24° C. for 2.5 hours. Additional methylene chloride was added and the solution was washed successively with dilute hydrochloric acid, dilute sodium bicarbonate solution and water. The residue obtained on concentration was eluted on 3-2000mu silica gel plates with 5percent acetone in methylene chloride. Starting material and the title compound were isolated. The latter, 376 mg., was identified by its nmr and mass spectra.
	In dichloromethane; acetone;	Step A (Route 3) A solution of the adamantyl amide from Example 24 (350 mg., 0.73 mmole), 2,6di-tert-butyl-4-methylpyridine (211 mg., 1.03 mmole) and trifluoromethane sulfonic anhydride (416 mg., 1.48 mmole) in 5 ml. of methylene chloride was prepared at 0° C. The mixture warmed to room temperature and was kept at 24° C. for 2.5 hours. Additional methylene chloride was added and the solution was washed successively with dilute hydrochloric acid, dilute sodium bicarbonate solution and water. The residue obtained on concentration was eluted on 3-2000mu silica gel plates with 5percent acetone in methylene chloride. Starting material and the title compound were isolated. The latter, 376 mg., was identified by its nmr and mass spectra.

Reference： [1]Patent: US5196411,1993,A
[2]Patent: US5075450,1991,A
[3]Patent: US5091380,1992,A

46
[ 38222-83-2 ]
1,2-cyclohexylidene-4,5,6-tri-O-benzyl-inositol [ No CAS ]
ammonium chloride [ No CAS ]
[ 149831-83-4 ]
1,2-cyclohexylidene-3-O-(5-phthalimidopentyl)-4,5,6-tri-O-benzyl-inositol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane;	B. 1,2-Cyclohexylidene-3-O-(5-phthalimidopentyl)-4,5,6-tri-O-benzyl-inositol(16). To a solution of 1,2-cyclohexylidene-4,5,6-tri-O-benzyl-inositol (9) (10.1 mmol) in dry dichloromethane (100 mL) is added <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (2.3 g, 11.1 mmol) and a solution of 5-phthalimido-1-pentyl triflate (15) (10.1 mmol) in dry dichloromethane (100 mL) at 0° C. To the resulting mixture is added sodium hydride (2.0 g, 50.5 mmol) and the reaction is stirred at room temperature for 24 h. The reaction is quenched by the addition of saturated aqueous ammonium chloride and extracted with dichloromethane. The combined extracts are dried over anhydrous sodium sulfate, concentrated in vacuo and purified by flash chromatography to afford 1,2-cyclohexylidene-3-O-(5-phthalimidopentyl)-4,5,6-tri-O-benzyl-inositol (16).

Reference： [1]Patent: US5550251,1996,A

47
[ 38222-83-2 ]
7-phthalimido-1-heptyl triflate [ No CAS ]
1,2-cyclohexylidene-4,5,6-tri-O-benzyl-inositol [ No CAS ]
ammonium chloride [ No CAS ]
1,2-cyclohexylidene-3-O-(7-phthalimidoheptyl)-4,5,6-tri-O-benzyl-inositol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane;	B. 1,2-Cyclohexylidene-3-O-(7-phthalimidoheptyl) -4,5,6-tri-O-benzyl-inositol (21). To a solution of 1,2-cyclohexylidene-4,5,6-tri-O-benzyl-inositol (9) (10.1 mmol) in dry dichloromethane (100 mL) is added <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (2.3 g, 11.1 mmol) and a solution of 7-phthalimido-1-heptyl triflate (20) (10.1 mmol) in dry dichloromethane (100 mL) at 0° C. To the resulting mixture is added sodium hydride (2.0 g, 50.5 mmol) and the reaction is stirred at room temperature for 24 h. The reaction is quenched by the addition of saturated aqueous ammonium chloride and extracted with dichloromethane. The combined extracts are dried over anhydrous sodium sulfate, concentrated in vacuo, and purified by flash chromatography to afford 1,2-cyclohexylidene-3-O-(7-phthalimidoheptyl)-4,5,6-tri-O-benzyl-inositol (21).

Reference： [1]Patent: US5550251,1996,A

48
[ 38222-83-2 ]
6-acetamido-1-hexyltriflate [ No CAS ]
1,2-cyclohexylidene-4,5,6-tri-O-benzyl-inositol [ No CAS ]
ammonium chloride [ No CAS ]
1,2-cyclohexylidene-3-O-(6-acetamidohexyl)-4,5,6-tri-O-benzyl-inositol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane;	B. 1,2-Cyclohexylidene-3-O-(6-acetamidohexyl)-4,5,6-tri-O-benzyl-inositol (26). To a solution of 1,2-cyclohexylidene-4,5,6-tri-O-benzyl-inositol (9) (10.1 mmol) in dry dichloromethane (100 mL) is added <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (2.3 g, 11.1 mmol) and a solution of 6-acetamido-1-hexyltriflate (25) (10.1 mmol) in dry dichloromethane (100 mL) at 0° C. To the resulting mixture is added sodium hydride (2.0 g, 50.5 mmol) and the reaction is stirred at room temperature for 24 h. The reaction is quenched by the addition of saturated aqueous ammonium chloride and extracted with dichloromethane. The combined extracts are dried over anhydrous sodium sulfate, concentrated in vacuo, and purified by flash chromatography to afford 1,2-cyclohexylidene-3-O-(6-acetamidohexyl)-4,5,6-tri-O-benzyl-inositol (26).

Reference： [1]Patent: US5550251,1996,A

49
[ 38222-83-2 ]
5-acetamido-1-pentyl triflate [ No CAS ]
1,2-cyclohexylidene-4,5,6-tri-O-benzyl-inositol [ No CAS ]
ammonium chloride [ No CAS ]
1,2-cyclohexylidene-3-O-(5-acetamidopentyl)-4,5,6-tri-O-benzyl-inositol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane;	B. 1,2-Cyclohexylidene-3-O-(5-acetamidopentyl)-4,5,6-tri-O-benzyl-inositol (31). To a solution of 1,2-cyclohexylidene-4,5,6-tri-O-benzyl-inositol (9) (10.1 mmol) in dry dichloromethane (100 mL) is added 2,6 -di-tert-butyl-4 -methylpyridine (2.3 g, 11.1 mmol) and a solution of 5-acetamido-1-pentyl triflate (30) (10.1 mmol) in dry dichloromethane (100 mL) at° C. To the resulting mixture is added sodium hydride (2.0 g, 50.5 mmol) and the reaction is stirred at room temperature for 24 h. The reaction is quenched by the addition of saturated aqueous ammonium chloride and extracted with dichloromethane. The combined extracts are dried over anhydrous sodium sulfate, concentrated in vacuo, and purified by flash chromatography to afford 1,2-cyclohexylidene-3-O-(5-acetamidopentyl)-4,5,6-tri-O-benzyl-inositol (31).

Reference： [1]Patent: US5550251,1996,A

50
[ 38222-83-2 ]
7-acetamido-1-heptyl triflate [ No CAS ]
1,2-cyclohexylidene-4,5,6-tri-O-benzyl-inositol [ No CAS ]
ammonium chloride [ No CAS ]
1,2-cyclohexylidene-3-O-(7-acetamidoheptyl)-4,5,6-tri-O-benzyl-inositol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane;	B. 1,2-Cyclohexylidene-3-O-(7-acetamidoheptyl) -4,5,6-tri-O-benzyl-inositol (36). To a solution of 1,2-cyclohexylidene-4,5,6-tri-O-benzyl-inositol (9) (10.1 mmol) in dry dichloromethane (100 mL) is added <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (2.3 g, 11.1 mmol) and a solution of 7-acetamido-1-heptyl triflate (35) (10.1 mmol) in dry dichloromethane (100 mL) at 0° C. To the resulting mixture is added sodium hydride (2.0 g, 50.5 mmol) and the reaction is stirred at room temperature for 24 h. The reaction is quenched by the addition of saturated aqueous ammonium chloride and extracted with dichloromethane. The combined extracts are dried over anhydrous sodium sulfate, concentrated in vacuo, and purified by flash chromatography to afford 1,2-cyclohexylidene-3-O-(7-acetamidoheptyl)-4,5,6-tri-O-benzyl-inositol (36).

Reference： [1]Patent: US5550251,1996,A

51
[ 38222-83-2 ]
6-Trimethylsiloxy-1-hexyltriflate [ No CAS ]
1,2-cyclohexylidene-4,5,6-tri-O-benzyl-inositol [ No CAS ]
ammonium chloride [ No CAS ]
1,2-cyclohexylidene-3-O-(6-trimethylsiloxyhexyl)-4,5,6-tri-O-benzyl-inositol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane;	B. 1,2-Cyclohexylidene-3-O-(6-trimethylsiloxyhexyl) -4,5,6-tri-O-benzyl-inositol (41). To a solution of 1,2-cyclohexylidene-4,5,6-tri-O-benzyl-inositol (9) (10.1 mmol) in dry dichloromethane (100 mL) is added <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (2.3 g, 11.1 mmol) and a solution of 6-trimethylsiloxy-1-hexyl triflate (40) (10.1 mmol) in dry dichloromethane (100 mL) at 0° C. To the resulting mixture is added sodium hydride (2.0 g, 50.5 mmol) and the reaction is stirred at room temperature for 24 h. The reaction is quenched by the addition of saturated aqueous ammonium chloride and extracted with dichloromethane. The combined extracts are dried over anhydrous sodium sulfate, concentrated in vacuo, and purified by flash chromatography to afford 1,2 -cyclohexylidene-3 -O- (6 -trimethylsiloxyhexyl) -4,5,6-tri-O-benzyl-inositol (41).

Reference： [1]Patent: US5550251,1996,A

52
[ 38222-83-2 ]
5-trimethylsiloxy-1-pentyl triflate [ No CAS ]
1,2-cyclohexylidene-4,5,6-tri-O-benzyl-inositol [ No CAS ]
ammonium chloride [ No CAS ]
1,2-cyclohexylidene-3-O-(5-trimethylsiloxypentyl)-4,5,6-tri-O-benzyl-inositol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane;	B. 1,2 - Cyclohexylidene-3-O- (5-trimethylsiloxypentyl) -4,5,6-tri-O-benzyl-inositol (46). To a solution of 1,2-cyclohexylidene-4,5,6-tri-O-benzyl-inositol (9) (10.1 mmol) in dry dichloromethane (100 mL) is added <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (2.3 g, 11.1 mmol) and a solution of 5-trimethylsiloxy-1-pentyl triflate (45) (10.1 mmol) in dry dichloromethane (100 mL) at 0° C. To the resulting mixture is added sodium hydride (2.0 g, 50.5 mmol) and the reaction is stirred at room temperature for 24 h. The reaction is quenched by the addition of saturated aqueous ammonium chloride and extracted with dichloromethane. The combined extracts are dried over anhydrous sodium sulfate, concentrated in vacuo, and purified by flash chromatography to afford 1,2-cyclohexylidene-3-O-(5-trimethylsiloxypentyl)-4,5,6-tri-O-benzyl-inositol (46).

Reference： [1]Patent: US5550251,1996,A

53
[ 38222-83-2 ]
7-trimethylsiloxy-1-heptyl triflate [ No CAS ]
1,2-cyclohexylidene-4,5,6-tri-O-benzyl-inositol [ No CAS ]
ammonium chloride [ No CAS ]
1,2-cyclohexylidene-3-O-(7-trimethylsiloxyheptyl)-4,5,6-tri-O-benzyl-inositol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane;	B. 1,2-Cyclohexylidene-3-O-(7-trimethylsiloxyheptyl) -4,5,6-tri-O-benzyl-inositol (51). To a solution of 1,2-cyclohexylidene-4,5,6-tri-O-benzyl-inositol (9) (10.1 mmol) in dry dichloromethane (100 mL) is added <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (2.3 g, 11.1 mmol) and a solution of 7-trimethylsiloxy-1-heptyl triflate (50) (10.1 mmol) in dry dichloromethane (100 mL) at 0° C. To the resulting mixture is added sodium hydride (2.0 g, 50.5 mmol) and the reaction is stirred at room temperature for 24 h. The reaction is quenched by the addition of saturated aqueous ammonium chloride and extracted with dichloromethane. The combined extracts are dried over anhydrous sodium sulfate, concentrated in vacuo, and purified by flash chromatography to afford 1,2-cyclohexylidene-3-O- (7-trimethylsiloxyheptyl) -4,5,6-tri-O-benzyl-inositol (51).

Reference： [1]Patent: US5550251,1996,A

54
[ 38222-83-2 ]
1,2-cyclohexylidene-4,5,6-tri-O-benzyl-inositol [ No CAS ]
ammonium chloride [ No CAS ]
[ 156631-29-7 ]
1,2-cyclohexylidene-3-O-(heptyl)-4,5,6-tri-O-benzyl-inositol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane;	A. 1,2-Cyclohexylidene-3-O-(heptyl)-4,5,6-tri-O-benzyl-inositol (63). To a solution of 1,2-cyclohexylidene-4,5,6-tri-O-benzyl-inositol (9) (10.1 mmol) in dry dichloromethane (100 mL) is added <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (2.3 g, 11.1 mmol) and a solution of heptyl triflate (10.1 mmol) in dry dichloromethane (100 mL) at 0° C. To the resulting mixture is added sodium hydride (2.0 g, 50.5 mmol) and the reaction is stirred at room temperature for 24 h. The reaction is quenched by the addition of saturated aqueous ammonium chloride and extracted with dichloromethane. The combined extracts are dried over anhydrous sodium sulfate, concentrated in vacuo, and purified by flash chromatography to afford 1,2-cyclohexylidene-3-O-(heptyl)-4,5,6-tri-O-benzyl-inositol (63).

Reference： [1]Patent: US5550251,1996,A

55
[ 38222-83-2 ]
1,2-cyclohexylidene-4,5,6-tri-O-benzyl-inositol [ No CAS ]
[ 53059-88-4 ]
ammonium chloride [ No CAS ]
1,2-cyclohexylidene-3-O-(hexyl)-4,5,6-tri-O-benzyl-inositol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane;	A. 1,2-Cyclohexylidene-3-O-(hexyl)-4,5,6-tri -O-benzyl-inositol (55). To a solution of 1,2-cyclohexylidene-4,5,6-tri-O-benzyl-inositol (9) (10.1 mmol) in dry dichloromethane (100 mL) is added <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (2.3 g, 11.1 mmol) and a solution of hexyl triflate (10.1 mmol) in dry dichloromethane (100 mL) at 0° C. To the resulting mixture is added sodium hydride (2.0 g, 50.5 mmol) and the reaction is stirred at room temperature for 24 h. The reaction is quenched by the addition of saturated aqueous ammonium chloride and extracted with dichloromethane. The combined extracts are dried over anhydrous sodium sulfate, concentrated in vacuo, and purified by flash chromatography to afford 1,2-cyclohexylidene-3-O-(hexyl)-4,5,6-tri-O-benzyl-inositol (55).

Reference： [1]Patent: US5550251,1996,A

56
[ 38222-83-2 ]
[ 152380-07-9 ]
1,2,4,5-bis-cyclohexylidene-6-O-benzyl-inositol [ No CAS ]
ammonium chloride [ No CAS ]
1,2,4,5-bis-cyclohexylidene-3-O-(6-phthalimidohexyl)-6-O-benzyl-inositol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane;	C. 1,2,4,5-bis-Cyclohexylidene-3-O-(6-phthalimidohexyl)-6-O-benzyl-inositol (69). To a solution of 1,2,4,5-bis-cyclohexylidene-6-O-benzyl-inositol (68) (10.1 mmol) in dry dichloromethane (100 mL) is added <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (2.3 g, 11.1 mmol) and a solution of 6-phthalimido-1-hexyl triflate (25) (10.1 mmol) in dry dichloromethane (100 mL) at 0° C. To the resulting mixture is added sodium hydride (2.0 g, 50.5 mmol) and the reaction is stirred at room temperature for 24 h. The reaction is quenched by the addition of saturated aqueous ammonium chloride and extracted with dichloromethane. The combined extracts are dried over anhydrous sodium sulfate, concentrated in vacuo, and purified by flash chromatography to afford 1,2,4,5-bis-cyclohexylidene-3-O-(6-phthalimidohexyl)-6-O-benzyl-inositol (69).

Reference： [1]Patent: US5550251,1996,A

57
[ 38222-83-2 ]
[ 4099-85-8 ]
[ 333-27-7 ]
[ 33985-44-3 ]

Yield	Reaction Conditions	Operation in experiment
61%	In dichloromethane;	Methyl 5-O-methyl-2,3-O-(1-methylethylidene)-beta-D-ribofuranoside. Methyl 2,3-O-(1-methylethylidene)-beta-D-ribofuranoside (13.3 g, 60 mmol), 2,6-di-t-butyl-4-methylpyridine (20.0 g, 100 mmol) and methyl trifluoromethylsulfonate (16.0 g, 100 mmol) were dissolved in dry dichloromethane (150 ml) placed in a closed reactor and heated to 80° C. After cooling, the reaction mixture was poured onto ice (150 ml). After standing, the product was extracted into dichloromethane (2*100 ml) and the combined extracts were dried (MgSO4) and evaporated in vacuo. The residue was purified by flash chromatography eluding with a mixture of cyclohexane and ethyl acetate (3:1) to afford methyl 5-O-methyl-2,3-O-(1-methylethylidene)-beta-D-ribofuranoside (8.0 g, 61percent) as an oil. 1 H-NMR (400 MHz, CDCl3) delta1.30 (3H, s, --CH3), 1.50 (3H, s, --CH3), 3.32 (3H, s, --OCH3), 3.39 (3H, s, --OCH3), 3.35-3.45 (2H, m, H-5a and H-5b), 4.30 (1H, t, H-4), 4.57 (1H, d, H-3), 4.65 (1H, d, H-2), 4.97 (1H, s, H-1).

Reference： [1]Patent: US5589467,1996,A

58
[ 38222-83-2 ]
[ 144-55-8 ]
[ 155044-88-5 ]
[ 164026-05-5 ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoromethylsulfonic anhydride; In dichloromethane;	D. Methyl 2,3,4-tri-O-benzyl-6-O-trifluoromethylsulfonyl-beta-D-glucopyranoside To a stirred solution of methyl 6-O-tert-butyldiphenylsilyl-2,3,4-tri-O-benzyl-beta-D-glucopyranoside (800 mg, 1.71 mmol) in 8.55 mL of dry dichloromethane at -78° C. was added 2,6-di-tert-butyl-4-methyl pyridine (632 mg, 3.08 mmol) followed by triflic anhydride (345 mul, 2.05 mmol). After stirring 15 minutes at -78° C., the mixture was warmed to room temperature over 20 minutes, and then poured into a solution of saturated aqueous NaHCO3 (20 mL) and extracted with ethyl acetate (50 mL). The organic layer was washed with saturated NaHCO3 (320 mL), saturated aqueous NaCl (120 mL), and dried over magnesium sulfate. Concentration provided crude target compound, which was used in the next step without further purification.

Reference： [1]Patent: US5811512,1998,A

59
[ 38222-83-2 ]
[ 89644-52-0 ]
[ 19243-04-0 ]
[ 22509-74-6 ]
7-acetamido-1-heptyl triflate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoromethylsulfonic anhydride; In dichloromethane; benzene;	A. 7-Acetamido-1-heptyl triflate (35). To a solution of 7-amino-1-heptanol (42.7 mmol) in benzene (100 mL) is added N-carbethoxyphthalimide (10.3 g, 47.0 mmol). The solution is stirred at room temperature for 5 h. The solvent is removed in vacuo to provide an oil, which is purified by flash chromatography. To a solution of 7-acetamido-1-heptanol (22.2 mmol) in dry dichloromethane (50 mL) is added <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (4.6 g, 22.2 mmol) and triflic anhydride (3.7 mL, 22.2 mmol) at 0° C. The reaction is stirred at room temperature for 20 min, poured into water, and extracted with dichloromethane. The combined extracts are dried over anhydrous sodium sulfate and concentrated in vacuo and to afford 7-acetamido-1-heptyl triflate (35) which is used without further purification.

Reference： [1]Patent: US5550251,1996,A

60
[ 38222-83-2 ]
[ 63273-48-3 ]
[ 149831-83-4 ]
[ 149831-91-4 ]
[ 149831-92-5 ]

Yield	Reaction Conditions	Operation in experiment
78%	With trifluoromethylsulfonic anhydride; In dichloromethane;	A stirred solution of 5-phthalimido-1-pentanol (III-33) (39.1 mg, 0.168 mmol) and <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (34.5 mg, 0.168 mmol) in dry dichloromethane (1.5 ml) was treated with triflic anhydride (28.3 ml, 0.168 mmol). After 10 min at room temperature, the mixture was diluted with water (25 ml) and extracted with dichloromethane (250 ml). The combined extracts were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo, affording a yellow solid which was used without purification in the next reaction. Sodium hydride (60percent dispersion in oil, 51 mg, 1.3 mmol) was added to a solution of alcohol III-44 (150 mg, 0.240 mmol), 5-phthalimidopentyl triflate (1.37 mmol), and <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (282 mg, 1.39 mmol), in dichloromethane (1.5 ml) at 0° C. The reaction mixture was stirred for 48 h at room temperature, quenched with saturated aqueous ammonium chloride, and extracted with dichloromethane, and the organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (20percent ethyl acetate/petroleum ether) gave III-45 (158 mg, 78percent yield) as a colorless oil: [alpha]D25 -2.5° (c 0.36, acetonitrile); UV (2.1410-4 M, acetonitrile) lambdamax 283.6 (epsilon710), 242.4 (808) nm; IR (CHCl3) 2940 (m), 2860 (m), 1775 (m), 1715 (s), 1450 (m), 1400 (s), 1370 (s), 1175 (m), 1120 (s), 1090 (s), 1050 (s), 745 (m), 720 (s), 700 (m) cm-1; 1 H NMR (500 MHz, CDCl3) delta7.96 (d, J=8.3 Hz, 1H), 7.84-7.80 (m, 4H), 7.69-7.64 (m, 2H), 7.50-7.17 (m, 12H), 4.69 (d, J=11.0 Hz, 1H), 4.67 (s, 2H), 4.64 (d, J=11.0 Hz, 1H), 4.36 (d, J=7.7 Hz, 1H), 4.21-4.17 (m, 1H), 3.86-3.81 (m, 1H), 3.66 (t, J=7.3 Hz, 2H), 3.60-3.39 (m, 6H), 3.28 (dd, J=7.8, 8.8 Hz, 1H), 3.00 (t, J=6.7 Hz, 2H), 2.12 (dd, J=5.4, 12.2 Hz, 1H), 1.71-1.58 (m, 5H), 1.47-1.36 (m, 3H); 13 C NMR (125 MHz, CDCl3) delta168.37, 138.61, 138.31, 135.19, 133.83, 133.56, 132.13, 131.03, 129.11, 128.31, 128.19, 127.96, 127.63, 127.51, 127.44, 126.65, 124.68, 123.51, 123.12, 119.78, 119.49, 113.70, 103.85, 82.83, 78.23, 74.90, 73.10, 72.16, 71.39, 70.95, 68.68, 37.86, 33.94, 29.67, 29.11, 28.36, 25.75, 23.41; high resolution mass spectrum (FAB, m-nitrobenzyl alcohol) m/z 865.3201 [(M+Na)+; calcd for C49 H50 N2 O9 SNa: 865.3134].

Reference： [1]Patent: US5552534,1996,A

61
[ 38222-83-2 ]
[ 2508-29-4 ]
[ 22509-74-6 ]
[ 63273-48-3 ]
[ 149831-83-4 ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoromethylsulfonic anhydride; In dichloromethane; benzene;	A. 5-Phthalimido-1-pentyl triflate (15). To a solution of 5-aminopentanol (42.7 mmol) in benzene (100 mL) is added N-carbethoxyphthalimide (10.3 g, 47.0 mmol). The solution is stirred at room temperature for 5 h. The solvent is removed in vacuo to provide an oil, which is purified by flash chromatography. To a solution of 5-phthalimido-1-pentanol (22.2 mmol) in dry dichloromethane (50 mL) is added <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (4.6 g, 22.2 mmol) and triflic anhydride (3.7 mL, 22.2 mmol) at 0° C. The reaction is stirred at room temperature for 20 min, poured into water, and extracted with dichloromethane. The combined extracts are dried over anhydrous sodium sulfate and concentrated in vacuo and to afford 5-phthalimido-1-pentyl triflate (15) which is used without further purification.

Reference： [1]Patent: US5550251,1996,A

62
[ 38222-83-2 ]
[ 63273-48-3 ]
[ 149831-83-4 ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoromethylsulfonic anhydride; In dichloromethane;	L. 5-Phthalimido-1-O-trifluoromethanesulfonylpentanol To a solution of 5-phthalimido-1-pentanol (39.1 mg, 0.168 mmol) in dry dichloromethane (1.5 mL) was added <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (34.5 mg, 0.168 mmol) followed by triflic anhydride (28.3 mug, 0.168 mmol). The solution was stirred at room temperature for 10 minutes. The reaction was poured into water (25 mL) and extracted with dichloromethane (2*50 mL). The organic layer was washed with a saturated sodium chloride solution and dried with anhydrous sodium sulfate. The solvents were removed under reduced pressure to yield a pale yellow solid which was used immediately without further purification.

Reference： [1]Patent: US5811512,1998,A

63
[ 38222-83-2 ]
[ 63273-48-3 ]
[ 149831-84-5 ]

Yield	Reaction Conditions	Operation in experiment
86%	With trifluoromethylsulfonic anhydride; In dichloromethane;	A stirred solution of 5-phthalimido-1-pentanol (III-33) (1.32 g, 4.67 mmol) and <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (0.960 g, 4.67 mmol) in dry dichloromethane (10 ml) was treated with triflic anhydride (0.784 ml, 4.67 mmol). After 10 min at room temperature, the mixture was diluted with water (100 ml) and extracted with dichloromethane (2200 ml). The combined extracts were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo, affording a yellow solid which was used without purification in the next reaction. Sodium hydride (60percent dispersion in oil, 0.20 g, 5.06 mmol) was added to a solution of alcohol III-32 (1.27 g, 3.89 mmol), 5-phthalimdopentyl triflate (4.67 mmol), and 15-crown-5 (20 mg, 2.3 mol percent), in dichloromethane (100 ml) at 0° C. After stirring for 24 h at room temperature, the mixture was poured into water. The aqueous layer was extracted with dichloromethane (350 ml) and the combined extracts were washed with water, dried over magnesium sulfate and concentrated in vacuo. Flash chromatography (3percent ether/dichloromethane) provided III-34 (1.82 g, 86percent yield) as a colorless oil: [alpha]D25 -8.2° (c 0.70, CHCl3); IR (CHCl3) 3080 (w), 3020 (m), 3009 (m), 2959 (m), 2880 (m), 1780 (m), 1719 (s), 1652 (m), 1500 (w), 1470 (w), 1457 (m), 1440 (m), 1400 (s), 1365 (m), 1235 (m), 1110 (br, s), 1058 (br, s), 908 (w), 692 (m), cm-1; 1 H NMR (500 MHz, CDCl3) delta7.80 (m, 2H), 7.68 (m, 2H), 7.25-7.34 (m, 10H), 6.38, (dd, J=6.1, 1.2 Hz, 1H), 4.84 (m, 2H), 4.66 (d, J=11.4 Hz, 1H), 4.63 (d, J=11.7 Hz, 1H), 4.55 (d, J=11.7 Hz, 1H), 4.19 (m, 1H), 4.00 (m, 1H), 3.81 (dd, J=8.7, 6.2 Hz, 1H), 3.64-3.74 (m, 4H), 3.40-3.50 (m, 2H), 1.60-1.70 (m, 4H), 1.40 (m, 2H); 13 C NMR (62.9 MHz, CDCl3) delta168.4, 144.8, 138.4, 138.3, 133.9, 132.2, 128.4, 127.9, 127.8, 127.6, 123.2, 99.9, 76.8, 75.8, 74.5, 73.8, 71.4, 70.5, 69.2, 37.9, 29.2, 28.5, 23.5; high resolution mass spectrum (Cl, NH3) m/z 541.2483 (M+; calcd for C33 H35 NO6: 541.2464).

Reference： [1]Patent: US5552534,1996,A

64
[ 1026737-34-7 ]
2-(N-Phenylsulfonylindol-3-yl)ethyl 3-Deoxy-2,4-di-O-benzyl-b-D-glucopyranoside [ No CAS ]
[ 38222-83-2 ]
[ 34626-51-2 ]
[ 170220-11-8 ]
2-(N-Phenylsulfonylindol-3-yl)-ethyl 2,4-Di-O-benzyl-3-deoxy-6-O-(5-azidopentyl)-β-D-glucopyranoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With trifluoromethylsulfonic anhydride; In dichloromethane; dimethyl sulfoxide;	Z. 2-(N-Phenylsulfonylindol-3-yl)ethyl 2,4-Di-O-benzyl-3-deoxy-6-O-(5-azidopentyl)-beta-D-glucopyranoside (III-29a). A stirred solution of 5-bromo-1-pentanol (0.79 g, 4.7 mmol) in DMSO (15 ml) was treated with sodium azide (1.83 g, 28.2 mmol). The resultant mixture was stirred at room temperature for 2.5 h, diluted with water, and extracted with diethyl ether. The combined organic layers were washed with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The azide was used without purification in the next step. Crude 5-azido-1-pentanol (280 mg, equivalent to 2.17 mmol) and <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (441 mg, 2.17 mmol) were dissolved in dichloromethane (9 ml) and triflic anhydride (0.36 ml, 2.17 mmol) was added dropwise. After 10 min the mixture was poured into brine (40 ml) and extracted with dichloromethane (2*40 ml). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. The triflate was used without purification in the next step. Sodium hydride (16 mg, 0.40 mmol, 60percent dispersion in oil) was added to a solution of alcohol III-28 (120 mg, 0.198 mmol) and azido triflate (105 mg, equivalent to 0.40 mmol) in dichloromethane (3 ml) at room temperature. The mixture was stirred for 24 h, diluted with dichloromethane (40 ml) and poured into saturated ammonium chloride (40 ml). The aqueous phase was extracted with dichloromethane and the combined organic solutions were washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (15percent ethyl acetate/hexane) afforded III-29a (121 mg, 83percent yield) as a colorless oil: [alpha]D25 +4.0° (c 0.24, CHCl3); IR (CHCl3) 3022 (s), 2940 (s), 2880 (m), 2105 (s), 1455 (s), 1375 (s), 1270 (s), 1210 (m), 1180 (m), 1125 (m), 1090 (m), 725 (s), 599 (m) cm-1; 1 H NMR (500 MHz, CDCl3) delta7.96 (d, J=8.1 Hz, 1H), 7.82 (dd, J=8.2, 0.9 Hz, 2H), 7.50-7.43 (m, 3H), 7.29-7.19 (m, 14H), 4.65 (d, J=12.0 Hz, 1H), 4.58 (d, J=11.4 Hz, 1H), 4.52 (d, J=12.0 Hz, 1H). 4.42 (d, J=11.5 Hz, 1H), 4.18 (dt, J=9.5, 6.7 Hz, 1H), 3.81 (dt, J=9.5, 7.1 Hz, 1H), 3.71 (d, J=10.6 Hz, 1H), 3.57 (dd, J=10.8, 4.7 Hz, 1H), 3.51-3.38 (m, 4H), 3.31-3.21 (m, 1H), 3.16 (t, J=6.9 Hz, 2H), 3.00 (t, J=6.9 Hz, 2H), 2.50-2.46 (dt, J=12.1, 4.5 Hz, 1H),1.63-1.50 (m, 5H), 1.48-1.32 (m, 3H); 13 C NMR (62.5 MHz, CDCl3) delta138.52, 138.23, 137.00, 135.07, 133.59, 131.09, 129.14, 128.43, 128.31, 127.78, 127.68, 127.50, 126.70, 126.69, 124.70, 123.54, 123.09, 119.71, 119.48, 113.70, 105.26, 78.01, 74.92, 72.67, 72.25, 71.38, 71.24, 69.96, 68.41, 34.97, 29.62, 29.15, 28.66, 25.65, 23.39; high resolution mass spectrum (FAB, m-nitrobenzyl alcohol) m/z 761.2973 (M+; calcd for C41 H46 N4 O7 S: 761.2985).

Reference： [1]Patent: US5552534,1996,A

65
[ 38222-83-2 ]
[ 146292-90-2 ]
[ 170219-86-0 ]

Yield	Reaction Conditions	Operation in experiment
89%	With NaH; trifluoromethylsulfonic anhydride; In dichloromethane; ethyl acetate;	L. Azide (-)-I-35. 6-Azidohexyl triflate I-34 was prepared as follows: A stirred solution of 6-azido-1-hexanol (0.17 g, 1.17 mmol) and <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (0.24 g, 1.17 mmol) in dry dichloromethane (10 ml) was treated with triflic anhydride (0.19 ml, 1.17 mmol). After 10 min at room temperature, the mixture was diluted with water (50 ml) and extracted with dichloromethane (325 ml). The combined extracts were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo, affording a yellow solid which was used without purification in the next reaction. To a solution of alcohol I-33 (0.54 g, 0.78 mmol) in dry CH2 Cl2 (30 ml) at 0° C. was added NaH (60percent, 0.050 g, 1.17 mmol) and 15-crown-5 (5 mg). After stirring for 20 minutes, triflate 34 (0.32 g, 1.17 mmol) as a solution in CH2 Cl2 (2 ml) was added via cannula. The mixture was stirred for an additional 24 h, quenched with water (30 ml) and the layers were separated. The aqueous layer was further extracted with CH2 Cl2 (320 ml) and the combined extracts were washed with water, dried over magnesium sulfate and concentrated in vacuo. Flash chromatography (12 percent ethyl acetate/ptroleum ether) provided I-35 (0.57 g, 89percent yield) as a colorless oil: [alpha]D25 -14.6° (c 1.22, CHCl3); IR (CHCl3) 3075 (w), 3017 (w), 2955 (s), 2880 (s), 2105 (s), 1450 (m), 1375 (m), 1275 (br, w), 1180 (s), 1125 (s), 1097 (s), 1070 (s), 975 (w), 885 (w), 810 (w), 670 (br, w), 600 (m), 570 (m) cm-1; 1 H NMR (500 MHz, CDCl3) delta1.03 (s, 21H), 1.31 (m, 4H), 1.51 (m, 5H), 2.40 (dt, J=12.3, 4.7 Hz, 1H), 2.98 (t, J=7.2 Hz, 2H), 3.15 (t, J=6.9 Hz, 2H), 3.40 (m, 4H), 3.56 (m, 2H), 3.77 (m, 2H), 4.09 (m, 1H), 4.24 (d, J=7.3 Hz, 1H), 4.48 (d, J=11.6 Hz, 1H), 4.59 (d, J=11.6 Hz, 1H), 7.22 (t, J=7.6 Hz, 1H), 7.25 (s, 1H), 7.30 (m, 5H), 7.40 (m, 3H), 7.47 (m, 2H), 7.84 (d, J=7.9 Hz, 2H), 7.96 (d, J=8.4 Hz, 1H); 13 C NMR (62.9 MHz, CDCl3) delta12.4, 18.0, 25.6, 25.7, 26.6, 28.8, 29.5, 38.3, 51.4, 68.5, 69.4, 70.1, 71.4, 71.5, 72.3, 78.1, 105.6, 113.7, 119.4, 119.7, 123.1, 123.4, 124.7, 126.8, 127.8, 128.4, 129.3, 131.1, 133.6, 135.2, 138.2, 138.3; high resolution mass spectrum (FAB, m-nitrobenzyl alcohol) m/z 853.3835[(M+Cl)+; calcd for C44 H62 SiSO7 N4 Cl: 853.3797).
89%	With NaH; trifluoromethylsulfonic anhydride; In dichloromethane; ethyl acetate;	L. Azide (-)-I-35. 6-Azidohexyl triflate I-34 was prepared as follows: A stirred solution of 6-azido-1-hexanol (0.17 g, 1.17 mmol) and <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (0.24 g, 1.17 mmol) in dry dichloromethane (10 ml) was treated with triflic anhydride (0.19 ml, 1.17 mmol). After 10 min at room temperature, the mixture was diluted with water (50 ml) and extracted with dichloromethane (325 ml). The combined extracts were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo, affording a yellow solid which was used without purification in the next reaction. To a solution of alcohol I-33 (0.54 g, 0.78 mmol) in dry CH2 Cl2 (30 ml) at 0° C. was added NaH (60percent, 0.050 g, 1.17 mmol) and 15-crown-5 (5 mg). After stirring for 20 minutes, triflate 34 (0.32 g, 1.17 mmol) as a solution in CH2 Cl2 (2 ml) was added via cannula. The mixture was stirred for an additional 24 h, quenched with water (30 ml) and the layers were separated. The aqueous layer was further extracted with CH2 Cl2 (320 ml) and the combined extracts were washed with water, dried over magnesium sulfate and concentrated in vacuo. Flash chromatography (12percent ethyl acetate/petroleum ether) provided I-35 (0.57 g, 89percent yield) as a colorless oil: [alpha]D25 -14.6° (c 1.22, CHCl3); IR (CHCl3) 3075 (w), 3017 (w), 2955 (s), 2880 (s), 2105 (s), 1450 (m), 1375 (m), 1275 (br, w), 1180 (s), 1125 (s), 1097 (s), 1070 (s), 975 (w), 885 (w), 810 (w), 670 (br, w), 600 (m), 570 (m) cm-1; 1 H NMR (500 MHz, CDCl3) delta 1.03 (s, 21H), 1.31 (m, 4H), 1.51 (m, 5H), 2.40 (dt, J=12.3, 4.7 Hz, 1H), 2.98 (t, J=7.2 Hz, 2H), 3.15 (t, J=6.9 Hz, 2H), 3.40 (m, 4H), 3.56 (m, 2H), 3.77 (m, 2H), 4.09 (m, 1H), 4.24 (d, J=7.3 Hz, 1H), 4.48 (d, J=11.6 Hz, 1H), 4.59 (d, J=11.6 Hz, 1H), 7.22 (t, J=7.6 Hz, 1H), 7.25 (s, 1H), 7.30 (m, 5H), 7.40 (m, 3H), 7.47 (m, 2H), 7.84 (d, J=7.9 Hz, 2H), 7.96 (d, J=8.4 Hz, 1H); 13 C NMR (62.9 MHz, CDCl3) delta 12.4, 18.0, 25.6, 25.7, 26.6, 28.8, 29.5, 38.3, 51.4, 68.5, 69.4, 70.1, 71.4, 71.5, 72.3, 78.1, 105.6, 113.7, 119.4, 119.7, 123.1, 123.4, 124.7, 126.8, 127.8, 128.4, 129.3, 131.1, 133.6, 135.2, 138.2, 138.3; high resolution mass spectrum (FAB, m-nitrobenzyl alcohol) m/z 853.3835(M+Cl)+; calcd for C44 H62 SiSO7 N4 Cl: 853.3797).

Reference： [1]Patent: US5552534,1996,A
[2]Patent: US5811512,1998,A

66
[ 38222-83-2 ]
[ 149831-78-7 ]
[ 155044-83-0 ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoromethylsulfonic anhydride; In dichloromethane;	H. 2-(1phenylsulfonyl-indol-3yl)ethyl-2,3,4-tri-O-benzyl-6-O-trifluoromethylsulfonyl-beta-D-glucopyranoside To a stirred solution of 2-(1-phenylsulfonyl-indol-3yl)ethyl-2,3,4-tri-O-benzyl-beta-D-glucopyranoside (196 mg, 0.27 mmol) in 2.7 mL of dry dichloromethane at -78° C. was added 2,6-di-tert-butyl-4-methyl pyridine (880 mg, 0.427 mmol) followed by triflic anhydride (58 mul, 0.347 mmol). After stirring 15 minutes at -78° C., the mixture was warmed to room temperature over 20 minutes, and then poured into saturated aqueous NaHCO3 (20 mL) and extracted with ethyl acetate (60 mL). The organic layer was washed with saturated aqueous NaHCO3 (320 mL), saturated aqueous NaCl (120 mL) and dried over magnesium sulfate. Concentration provided the crude triflate target compound, which used in the next step without purification.
	With trifluoromethylsulfonic anhydride; In dichloromethane;	H. 2-(1Phenylsulfonyl-indol-3yl)ethyl-2,3,4-tri-O-benzyl-6-O-trifluoromethylsulfonyl-beta-D-glucopyranoside To a stirred solution of 2-(1-phenylsulfonyl-indol-3yl)ethyl-2,3,4-tri-O-benzyl-beta-D-glucopyranoside (196 mg, 0.27 mmol) in 2.7 mL of dry dichloromethane at -78° C. was added 2,6-di-tert-butyl-4-methyl pyridine (880 mg, 0.427 mmol) followed by triflic anhydride (58 mul, 0.347 mmol). After stirring 15 minutes at -78° C., the mixture was warmed to room temperature over 20 minutes, and then poured into saturated aqueous NaHCO3 (20 mL) and extracted with ethyl acetate (60 mL). The organic layer was washed with saturated aqueous NaHCO3 (320 mL), saturated aqueous NaCl (120 mL) and dried over magnesium sulfate. Concentration provided the crude triflate target compound, which used in the next step without purification.

Reference： [1]Patent: US5552534,1996,A
[2]Patent: US5811512,1998,A

67
[ 38222-83-2 ]
[ 23363-92-0 ]
6-acetamido-1-hexyltriflate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoromethylsulfonic anhydride; In dichloromethane;	To a solution of 6-acetamido-1-hexanol (22.2 mmol) in dry dichloromethane (50 mL) is added <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (4.6 g, 22.2 mmol) and triflic anhydride (3.7 mL, 22.2 mmol) at 0° C. The reaction is stirred at room temperature for 20 min, poured into water, and extracted with dichloromethane. The combined extracts are dried over anhydrous sodium sulfate and concentrated in vacuo and to afford 6-acetamido-1-hexyltriflate (25) which is used without further purification.

Reference： [1]Patent: US5550251,1996,A

68
[ 38222-83-2 ]
[ 2508-29-4 ]
[ 40447-15-2 ]
5-acetamido-1-pentyl triflate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoromethylsulfonic anhydride; acetic anhydride; triethylamine; In methanol; dichloromethane;	A. 5-Acetamido-1-pentyl triflate (30). A solution of 5-amino-1-pentanol (0.650 g, 6.31 mmol) in methanol (15 mL) is cooled to 0° C. and treated with triethylamine (1.62 mL, 11.6 mmol) followed by acetic anhydride (0.891 mL, 9.45 mmol). The reaction mixture is stirred at room temperature overnight. Additional triethylamine (1.6 mL, 11.6 mmol) and acetic anhydride (0.9 mL, 9.5 mmol) is added at room temperature and the solution is stirred 16 h further. Concentration in vacuo and flash chromatography affords 5-acetamido-1-pentanol. To a solution of 5-acetamido-1-pentanol (22.2 mmol) in dry dichloromethane (50 mL) is added <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (4.6 g, 22.2 mmol) and triflic anhydride (3.7 mL, 22.2 mmol) at 0° C. The reaction is stirred at room temperature for 20 min, poured into water, and extracted with dichloromethane. The combined extracts are dried over anhydrous sodium sulfate and concentrated in vacuo and to afford 5-acetamido-1-pentyl triflate (30) which is used without further purification.

Reference： [1]Patent: US5550251,1996,A

69
[ 38222-83-2 ]
[ 5665-79-2 ]
6-Trimethylsiloxy-1-hexyltriflate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoromethylsulfonic anhydride; In dichloromethane;	To a solution of 6-trimethylsiloxy-1-hexanol (11.6 mmol) in dry dichloromethane (50 mL) is added <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (4.6 g, 22.2 mmol) and triflic anhydride (3.7 mL, 22.2 mmol) at 0° C. The reaction is stirred at room temperature for 20 min, poured into water, and extracted with dichloromethane. The combined extracts are dried over anhydrous sodium sulfate and concentrated in vacuo and to afford 6-trimethylsiloxy-1-hexyl triflate (40) which is used without further purification.

Reference： [1]Patent: US5550251,1996,A

70
[ 38222-83-2 ]
5-trimethylsiloxy-1-pentanol [ No CAS ]
5-trimethylsiloxy-1-pentyl triflate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoromethylsulfonic anhydride; In dichloromethane;	To a solution of 5-trimethylsiloxy-1-pentanol (11.6 mmol) in dry dichloromethane (50 mL) is added 2,6-di-tert-butyl-4methylpyridine (4.6 g, 22.2 mmol) and triflic anhydride (3.7 mL, 22.2 mmol) at 0° C. The reaction is stirred at room temperature for 20 min, poured into water, and extracted with dichloromethane. The combined extracts are dried over anhydrous sodium sulfate and concentrated in vacuo and to afford 5-trimethylsiloxy-1-pentyl triflate (45) which is used without further purification.

Reference： [1]Patent: US5550251,1996,A

71
[ 38222-83-2 ]
7-trimethylsiloxy-1-heptanol [ No CAS ]
7-trimethylsiloxy-1-heptyl triflate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoromethylsulfonic anhydride; In dichloromethane;	To a solution of 7-trimethylsiloxy-1-heptanol (11.6 mmol) in dry dichloromethane (50 mL) is added <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (4.6 g, 22.2 mmol) and triflic anhydride (3.7 mL, 22.2 mmol) at 0° C. The reaction is stirred at room temperature for 20 min, poured into water, and extracted with dichloromethane. The combined extracts are dried over anhydrous sodium sulfate and concentrated in vacuo and to afford 7-trimethylsiloxy-1-heptyl triflate (50) which is used without further purification.

Reference： [1]Patent: US5550251,1996,A

72
[ 38222-83-2 ]
[ 401601-00-1 ]
7-phthalimido-1-heptyl triflate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoromethylsulfonic anhydride; In dichloromethane;	To a solution of 7-phthalimido-1-heptanol (22.2 mmol) in dry dichloromethane (50 mL) is added <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (4.6 g, 22.2 mmol) and triflic anhydride (3.7 mL, 22.2 mmol) at 0° C. The reaction is stirred at room temperature for 20 min, poured into water, and extracted with dichloromethane. The combined extracts are dried over anhydrous sodium sulfate and concentrated in vacuo and to afford 7-phthalimido-1-heptyl triflate (20) which is used without further purification.

Reference： [1]Patent: US5550251,1996,A

73
[ 38222-83-2 ]
[ 3282-30-2 ]
[ 108-24-7 ]
Methyl-6-deoxy-3,4-isopropylidene-2-O-(trimethylsilyl)-β-D-galactopyranoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoromethylsulfonic anhydride; sodium hydrogencarbonate; In dichloromethane;	To obtain resin 5, 3 (95.4 mg) is added to a solution of the sulfoxide 4 (122.1 mg, 0.156 mmol, 1.0 eq.) and 2,6-di-tert-butyl-4-methyl-pyridine (98.2 mg, 0.468 mmol, 3.0 eq.) in CH2 Cl2 (7.0 mL) and the suspension cooled to -78° C. After 10 mins, triflic anhydride (13.1 muL, 0.078 mmol, 0.5 eq.) in CH2 Cl2 (5.0 mL) is added dropwise over a period of 20 mins. Ten minutes after the addition is complete, the reaction is warmed to -60° C. over a period of 20 mins. The reaction is quenched by the addition of saturated NaHCO3. The resin is collected by suction filtration and washed with methanol (210 mL), water (110 mL), methanol (110 mL), and then CH2 Cl2 (1010 mL). The product resin 5 is then dried under vacuum overnight, after which the glycosylation is repeated. The product resin 6 is obtained as follows: resin 5 (112.7 mg) is washed with 10percent trifluoroacetic acid in CH2 Cl2 (20 mL). It is then washed with CH2 Cl2 (1010 mL) and dried under vacuum overnight. Then resin 7 is obtained from resin 6 as follows: resin 6 (110.7 mg) is added to a solution of sulfoxide 4 (123.5 mg, 0.158 mmol, 1.0 eq.) and 2,6-di-tert-butyl-4-methyl-pyridine (99.3 mg, 0.474 mmol, 3.0 eq.) in CH2 Cl2 (7.0 mL) and the suspension cooled to -78° C. After 10 mins, triflic anhydride (13.3 muL, 0.079 mmol, 0.5 eq.) in CH2 Cl2 (5.0 mL) is added dropwise over a period of 20 mins. Ten minutes after the addition is complete, the reaction is warmed to -60° C. over a period of 20 mins. The reaction is quenched by the addition of saturated NaHCO3. The resin is isolated by filtration and washed with methanol (210 mL), water (110 mL), methanol (110 mL), and then CH2 Cl2 (1010 mL). The product resin 7 is dried under vacuum overnight, after which the glycosylation is repeated. Finally, compound 8 is obtained from resin 7 as follows: resin 7 (113.6 mg) is washed with 10percent trifluoroacetic acid in CH2 Cl2 (20 mL). It is then washed with CH2 Cl2 (1010 mL) and suspended in pyridine (10 mL).

Reference： [1]Patent: US5700916,1997,A

74
[ 38222-83-2 ]
[ 158600-05-6 ]
[ 75-09-2 ]
[ 158600-06-7 ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoromethanesulfonic acid anhydride; In hexane;	(i) Methyl-17beta-[3-(4-trifluoromethylsulfonyloxyphenyl)propionyl]-estra-1,3,5(10)-triene-3-carboxylate. Trifluoromethanesulfonic anhydride (0.25 g, 0.9 mmoles) was added to a mixture of methyl-17beta-[3-(4-hydroxyphenyl)propionyl]-estra-1,3,5(10)-triene-3-carboxylate (0.27 g, 0.6 mmoles) (prepared according to Example 28(ii)), <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (0.15 g. 0.73 mmoles) and CH2 Cl2 (10 ml). After stirring for 4 hours at ambient temperature the reaction mixture was washed successively with ice-water, dil HCl, water, 5percent NaHCO3, brine, dried and concentrated. The resulting residue was chromatographed (silica gel) eluding with hexane then 10percent EtOAc in hexane to give the title compound (0.23 g).

Reference： [1]Patent: US5618806,1997,A

75
[ 38222-83-2 ]
petroleum-dichloromethane [ No CAS ]
[ 358-23-6 ]
[ 901-93-9 ]
[ 154229-39-7 ]

Yield	Reaction Conditions	Operation in experiment
78%	In dichloromethane;	(a) 3-Acetoxyestra-1,3,5[10],16-tetraen-17-yl trifluoromethanesulphonate The method followed that described in Example 1(a), but using oestrone-3-acetate (4.69 g, 15 mmol), dichloromethane (120 ml), 2,6-di-t-butyl-4-methylpyridine (4.00 g, 19.5 mmol), and trifluoromethanesulphonic anhydride (2.8 ml, 16.5 mmol). Chromatography, on elution with light petroleum-dichloromethane (3:1), afforded the title compound (5.21 g, 78percent). 1 H-NMR(CDCl3) inter alia delta1.00(3H,s,18-CH3), 2.29(3H,s,CH3 CO2), 5.62(1H,m, 16-H), 6.81(1H,m,ArH), 6.85(1H,m,ArH), 7.26(1H,m,ArH). Anal. Calcd. for C21 H23 O5 F3 S1.1/2H2 O: C, 55.62; H, 5.34. Found: C, 55.58: H, 5.14percent.

Reference： [1]Patent: US5604213,1997,A

76
[ 38222-83-2 ]
petroleum-dichloromethane [ No CAS ]
[ 358-23-6 ]
[ 103708-01-6 ]
[ 154229-37-5 ]

Yield	Reaction Conditions	Operation in experiment
30%	In dichloromethane;	(a) 3-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy]androsta-3,5,16-trien-17-yl trifluoromethanesulphonate The method followed that described in Example 1(a) but using 3-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy]androsta-3,5-dien-17-one (5.03 g, 10 mmol), prepared as described in M. Jarman and R. McCague, J. Chem. Soc., Perkin Trans. 1, 1129 (1987), dichloromethane (80 ml), 2,6-di-t-butyl-4-methylpyridine (2.87 g, 14 mmol), and trifluoromethanesulphonic anhydride (1.85 ml, 11 mmol). Chromatography, on elution with light petroleum-dichloromethane (10:1), afforded the title compound (1.93 g, 30percent) which crystallized from ethanol, m.p. 106°-107° C. 1 H-NMR (CDCl3) inter alia delta1.02(6H,s,18 and 19-CH3), 5.16(1H,s,4-H), 5.28(1H,m,6-H), 5.59(1H,m,16-H); MS m/z 634 (M+).

Reference： [1]Patent: US5604213,1997,A

77
[ 38222-83-2 ]
[ 166978-61-6 ]
[ 60-29-7 ]
[ 166978-62-7 ]

Yield	Reaction Conditions	Operation in experiment
85%	In dichloromethane;	EXAMPLE 125 Methyl 1,1-dimethyl-3-(trifluoromethanesulfonyloxy)-1H-indene-5-carboxylate STR119 To a solution of methyl 1,1-dimethyl-3-oxo-indan-5-carboxylate (0.90 g, 4.12 mmol) and <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (1.10 mg, 5.36 mmol) in 10 mL of methylene chloride was added triflic acid anhydride (1.39 g, 4.94 mmol) at -78° C. After being stirred at room temperature for 16 hours, the mixture was diluted with 70 mL of ethyl ether, washed with 1N HCl (20 mL), dried over magnesium sulfate, and evaporated. The residue was purified by flash chromatography (EtOAc:hexane=1:20 to 1:5) to give 1.23 g (85percent yield) of the title compound; 1 H NMR (CDCl3) delta1.41 (s, 6H),3.95 (s, 3H), 6.30 (s, 1H), 7.44 (d, J=7.8 Hz, 1H), 7.99 (s, 1H), 8.06 (d, J=7.8 Hz, 1H); MS m/e 351 (MH+).
85%	In dichloromethane;	EXAMPLE 125 Methyl 1,1-dimethyl-3-(trifluoromethanesulfonyloxy)-1H-indene-5-carboxylate STR119 To a solution of methyl 1,1-dimethyl-3-oxo-indan-5-carboxylate (0.90 g, 4.12 mmol) and <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (1.10 mg, 5.36 mmol) in 10 mL of methylene chloride was added triflic acid anhydride (1.39 g, 4.94 mmol) at -78° C. After being stirred at room temperature for 16 hours, the mixture was diluted with 70 mL of ethyl ether, washed with 1N HCl (20 mL), dried over magnesium sulfate, and evaporated. The residue was purified by flash chromatography (EtOAc:hexane=1:20 to 1:5) to give 1.23 g (85percent yield) of the title compound; 1 H NMR (CDCl3) delta 1.41 (s, 6H),3.95 (s, 3H), 6.30 (s, 1H), 7.44 (d, J=7.8 Hz, 1H), 7.99 (s, 1H), 8.06 (d, J=7.8 Hz, 1H); MS m/e 351 (MH+).

Reference： [1]Patent: US5618839,1997,A
[2]Patent: US5648385,1997,A

78
[ 38222-83-2 ]
[ 166978-69-4 ]
[ 166978-70-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	In dichloromethane;	EXAMPLE 135 Methyl 4-[1,1-dimethyl-3-(trifluoromethanesulfonyloxy)-1H-indene-5-yloxymethyl]benzoate STR129 To a solution of methyl 4-(1,1-dimethyl-3-oxo-indan-5-yloxymethyl)benzoate (675 mg, 2.08 mmol) and <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (534 mg, 2.60 mmol) in 5 mL of methylene chloride was added triflic acid anhydride (705 mg, 2.50 mmol) at -78° C. After being stirred at room temperature for 16 hours, the mixture was diluted with 1N HCl (20 mL), extracted with ethyl ether (20 mL*3). The combined extracts were dried over magnesium sulfate and evaporated. The residue was purified by flash chromatography (EtOAc:hexane=1:20 to 1:10) to give 849 mg (95percent yield) of the title compound as a solid; 1 H-NMR (CDCl3) delta1.37 (s, 6H), 3.93 (s, 1H), 5.15 (s, 2H), 6.24 (s, 1H), 6.90-6.94 (m, 2H), 7.25 (d over CHCl3, J=8.8 Hz, 1H), 7.53 (d, J=8.7 Hz, 2H), 8.08 (d, J=8.7 Hz, 2H); MS m/e 457 (MH+). Anal. calcd. for C21 H19 F3 O6 S: C, 55.26; H, 4.20. Found: C, 55.39; H, 4.08.
95%	In dichloromethane;	EXAMPLE 135 Methyl 4-[1,1-dimethyl-3-(trifluoromethanesulfonyloxy)-1H-indene-5-yloxymethyl]benzoate STR129 To a solution of methyl 4-(1,1-dimethyl-3-oxo-indan-5-yloxymethyl)benzoate (675 mg, 2.08 mmol) and <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (534 mg, 2.60 mmol) in 5 mL of methylene chloride was added triflic acid anhydride (705 mg, 2.50 mmol) at -78° C. After being stirred at room temperature for 16 hours, the mixture was diluted with 1N HCl (20 mL), extracted with ethyl ether (20 mL*3). The combined extracts were dried over magnesium sulfate and evaporated. The residue was purified by flash chromatography (EtOAc:hexane=1:20 to 1:10) to give 849 mg (95percent yield) of the title compound as a solid; 1 H-NMR (CDCl3) 8 1.37 (s, 6H), 3.93 (s, 1H), 5.15 (s, 2H), 6.24 (s, 1H), 6.90-6.94 (m, 2H), 7.25 (d over CHCl3, J=8.8 Hz, 1H), 7.53 (d, J=8.7 Hz, 2H), 8.08 (d, J=8.7 Hz, 2H); MS m/e 457 (MH+). Anal. calcd. for C21 H19 F3 O6 S: C, 55.26; H, 4.20. Found: C, 55.39; H, 4.08.

Reference： [1]Patent: US5618839,1997,A
[2]Patent: US5648385,1997,A

79
[ 38222-83-2 ]
[ 166978-72-9 ]
methyl [2-[1,1-dimethyl-3-(trifluoromethanesulfonyloxy)-1H-indene-5-yl]vinyl]benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	In dichloromethane;	EXAMPLE 140 Methyl [2-[1,1-dimethyl-3-(trifluoromethanesulfonyloxy)-1H-indene-5-yl]vinyl]benzoate STR134 To a solution of methyl 4-[2-(1,1-dimethyl-3-oxo-indan-5-yl)vinyl]benzoate (450 mg, 1.40 mmol) and <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (345 mg, 1.68 mmol) in 5 mL of methylene chloride was added triflic acid anhydride (434 mg, 1.54 mmol) at -78° C. After stirring at room temperature for 16 hours, the mixture was diluted with 1N HCl (20 mL), extracted with ethyl ether (20 mL*3). The combined extracts were dried over magnesium sulfate and evaporated. The residue was purified by flash chromatography (CH2 Cl2; hexane=1:2 to 1:1) to give 606 mg (95percent yield) of the title compound as a solid; 1 H-NMR (CDCl3) delta1.41 (s, 6H), 3.94 (s, 3H), 6.27 (s, 1H), 7.15 (d, J=16.3 Hz, 1H), 7.27 (d, J=16.3 Hz, 1H), 7.37 (d, J=8.2 Hz, 1H), 7.49 and 7.50 (d over s, J=8.2 Hz, 2H), 7.59 (d, J=8.4 Hz, 2H), 8.05 (d, J=8.4 Hz, 2H); (MS m/e 453 (MH+). Anal. calcd. for C22 H19 F3 O5 S: C, 58.40; H, 4.23. Found: C, 58.38; H, 4.00.
95%	In dichloromethane;	EXAMPLE 140 Methyl [2-[1,1-dimethyl-3-(trifluoromethanesulfonyloxy)-1H-indene-5-yl]vinyl]benzoate STR134 To a solution of methyl 4-[2-(1,1-dimethyl-3-oxo-indan-5-yl)vinyl]benzoate (450 mg, 1.40 mmol) and <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (345 mg, 1.68 mmol) in 5 mL of methylene chloride was added triflic acid anhydride (434 mg, 1.54 mmol) at -78° C. After stirring at room temperature for 16 hours, the mixture was diluted with 1N HCl (20 mL), extracted with ethyl ether (20 mL*3). The combined extracts were dried over magnesium sulfate and evaporated. The residue was purified by flash chromatography (CH2 Cl2; hexane=1:2 to 1:1) to give 606 mg (95percent yield) of the title compound as a solid; 1 H-NMR (CDCl3) delta 1.41 (s, 6H), 3.94 (s, 3H), 6.27 (s, 1H), 7.15 (d, J=16.3 Hz, 1H), 7.27 (dr J=16.3 Hz, 1H), 7.37 (d, J=8.2 Hz, 1H), 7.49 and 7.50 (d over s, J=8.2 Hz, 2H), 7.59 (d, J=8.4 Hz, 2H), 8.05 (d, J=8.4 Hz, 2H); (MS m/e 453 (MH+). Anal. calcd. for C22 H19 F3 O5 S: C, 58.40; H, 4.23. Found: C, 58.38; H, 4.00.

Reference： [1]Patent: US5618839,1997,A
[2]Patent: US5648385,1997,A

80
[ 38222-83-2 ]
[ 157977-53-2 ]
→ EtOAc [ No CAS ]
trifluoromethyl-17β-[3-(4-fluorophenyl)-1-oxopropyl]-androsta-3,5-diene-3-sulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With trifluoromethanesulfonic acid anhydride; In dichloromethane;	(iii) Trifluoromethyl-17beta-[3-(4-fluorophenyl)-1-oxopropyl]-androsta-3,5-diene-3-sulfonate To a solution of 17beta-[3-(4-fluorophenyl)-1-oxopropyl]-androst-4-ene-3-one (0.77 g, 1.8 mmol) and <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (0.51 g, 2.5 mmol) in CH2 Cl2 (20 mL) was slowly added trifluoromethanesulfonic anhydride (0.75 g, 2.7 mmol). After stirring for 2 hours at room temperature, the reaction mixture was washed with dilute HCl, water, dilute NaHCO3, brine, dried (MgSO4), filtered, concentrated in vacuo, and chromatographed (silica gel, hexanes 5percent --> EtOAc in hexanes) to give 0.44 g of white solid (44percent yield).

Reference： [1]Patent: US5641765,1997,A

81
[ 38222-83-2 ]
15-crown-S [ No CAS ]
[ 63273-48-3 ]
[ 149831-84-5 ]

Yield	Reaction Conditions	Operation in experiment
86%	With trifluoromethylsulfonic anhydride; In dichloromethane;	AG. 3,4-Di-O-Benzyl-6-O-(5-phthalimidopentyl)-D-glucal (III-34) 5-Phthalimidopentyl triflate was prepared as follows: A stirred solution of 5-phthalimido-1-pentanol (III-33) (1.32 g, 4.67 mmol) and <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (0.960 g, 4.67 mmol) in dry dichloromethane (10 ml) was treated with triflic anhydride (0.784 ml, 4.67 mmol). After 10 min at room temperature, the mixture was diluted with water (100 ml) and extracted with dichloromethane (2200 ml). The combined extracts were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo, affording a yellow solid which was used without purification in the next reaction. Sodium hydride (60percent dispersion in oil, 0.20 g, 5.06 mmol) was added to a solution of alcohol III-32 (1.27 g, 3.89 mmol), 5-phthalimdopentyl triflate (4.67 mmol), and 15-crown-S (20 mg, 2.3 mol percent), in dichloromethane (100 ml) at 0° C. After stirring for 24 h at room temperature, the mixture was poured into water. The aqueous layer was extracted with dichloromethane (350 ml) and the combined extracts were washed with water, dried over magnesium sulfate and concentrated in vacuo. Flash chromatography (3percent ether/dichloromethane) provided III-34 (1.82 g, 86percent yield) as a colorless oil: [alpha]D25 -8.20 (c 0.70, CHCl3); IR (CHCl3) 3080 (w), 3020 (m), 3009 (m), 2959 (m), 2880 (m), 1780 (m), 1719 (s), 1652 (m), 1500 (w), 1470 (w), 1457 (m), 1440 (m), 1400 (s), 1365 (m), 1235 (m), 1110 (br, s), 1058 (br, s), 908 (w), 692 (m), cm-1; 1 H NMR (500 MHz, CDCl3) delta7.80 (m, 2 H), 7.68 (m, 2 H), 7.25-7.34 (m, 10 H), 6.38, (dd, J=6.1, 1.2 Hz, 1 H), 4.84 (m, 2 H), 4.66 (d, J=11.4 Hz, 1 H), 4.63 (d, J=11.7 Hz, 1 H), 4.55 (d, J=11.7 Hz, 1 H), 4.19 (m, 1 H), 4.00 (m, 1 H), 3.81 (dd, J=8.7, 6.2 Hz, 1 H), 3.64-3.74 (m, 4 H), 3.40-3.50 (m, 2 H), 1.60-1.70 (m, 4 H), 1.40 (m, 2 H); 13 C NMR (62.9 MHz, CDCl3) delta168.4, 144.8, 138.4, 138.3, 133.9, 132.2, 128.4, 127.9, 127.8, 127.6, 123.2, 99.9, 76.8, 75.8, 74.5, 73.8, 71.4, 70.5, 69.2, 37.9, 29.2, 28.5, 23.5; high resolution mass spectrum (Cl, NH3) m/z 541.2483 (M+; calcd for C33 H35 NO6: 541.2464).

Reference： [1]Patent: US5811512,1998,A

82
[ 1026737-34-7 ]
2-(N-Phenylsulfonylindol-3-yl) ethyl 3-Deoxy-2,4-di-O-benzyl-β-D-glucopyranoside [ No CAS ]
[ 38222-83-2 ]
[ 34626-51-2 ]
[ 170220-11-8 ]
2-(N-Phenylsulfonylindol-3-yl) ethyl 2,4-Di-O-benzyl-3-deoxy-6-O-(5-azidopentyl)-β-D-glucopyranoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With trifluoromethylsulfonic anhydride; In dichloromethane; dimethyl sulfoxide;	Z. 2-(N-Phenylsulfonylindol-3-yl) ethyl 2,4-Di-O-benzyl-3-deoxy-6-O-(5-azidopentyl)-beta-D-glucopyranoside (III-29a) A stirred solution of 5-bromo-1-pentanol (0.79 g, 4.7 mmol) in DMSO (15 ml) was treated with sodium azide (1.83 g, 28.2 mmol). The resultant mixture was stirred at room temperature for 2.5 h, diluted with water, and extracted with diethyl ether. The combined organic layers were washed with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The azide was used without purification in the next step. Crude 5-azido-1-pentanol (280 mg, equivalent to 2.17 mmol) and <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (441 mg, 2.17 mmol) were dissolved in dichloromethane (9 ml) and triflic anhydride (0.36 ml, 2.17 mmol) was added dropwise. After 10 min the mixture was poured into brine (40 ml) and extracted with dichloromethane (2*40 ml). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. The triflate was used without purification in the next step. Sodium hydride (16 mg, 0.40 mmol, 60percent dispersion in oil) was added to a solution of alcohol III-28 (120 mg, 0.198 mmol) and azido triflate (105 mg, equivalent to 0.40 mmol) in dichloromethane (3 ml) at room temperature. The mixture was stirred for 24 h, diluted with dichloromethane (40 ml) and poured into saturated ammonium chloride (40 ml). The aqueous phase was extracted with dichloromethane and the combined organic solutions were washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (15percent ethyl acetate/hexane) afforded III-29a (121 mg, 83percent yield) as a colorless oil: [alpha]D25 +4.0° (c 0.24, CHCl3); IR (CHCl3) 3022 (s), 2940 (s), 2880 (m), 2105 (s), 1455 (s), 1375 (s), 1270 (s), 1210 (m), 1180 (m), 1125 (m), 1090 (m), 725 (s), 599 (m) cm-1; 1 H NMR (500 MHz, CDCl3) delta7.96 (d, J=8.1 Hz, 1 H), 7.82 (dd, J=8.2, 0.9 Hz, 2 H), 7.50-7.43 (m, 3 H), 7.29-7.19 (m, 14 H), 4.65 (d, J=12.0 Hz, 1 H), 4.58 (d, J=11.4 Hz, 1 H), 4.52 (d, J=12.0 Hz, 1 H), 4.42 (d, J=11.5 Hz, 1 H), 4.18 (dt, J=9.5, 6.7 Hz, 1 H), 3.81 (dt, J=9.5, 7.1 Hz, 1 H), 3.71 (d, J=10.6 Hz, 1 H), 3.57 (dd, J=10.8, 4.7 Hzr 1 H), 3.51-3.38 (m, 4 H), 3.31-3.21 (m, 1 H), 3.16 (t, J=6.9 Hz, 2 H), 3.00 (t, J=6.9 Hz, 2 H), 2.50-2.46 (dt, J=12.1, 4.5 Hz, 1 H),1.63-1.50 (m, 5 H), 1.48-1.32 (m, 3 H); 13 C NMR (62.5 MHz, CDCl3) delta138.52, 138.23, 137.00, 135.07, 133.59, 131.09, 129.14, 128.43, 128.31, 127.78, 127.68, 127.50, 126.70, 126.69, 124.70, 123.54, 123.09, 119.71, 119.48, 113.70, 105.26, 78.01, 74.92, 72.67, 72.25, 71.38, 71.24, 69.96, 68.41, 34.97, 29.62, 29.15, 28.66, 25.65, 23.39; high resolution mass spectrum (FAB, m-nitrobenzyl alcohol) m/z 761.2973 (M+; calcd for C41 H46 N4 O7 S: 761.2985).

Reference： [1]Patent: US5811512,1998,A

83
[ 38222-83-2 ]
[ 208253-11-6 ]
[ 208253-12-7 ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoromethanesulfonic acid anhydride; In dichloromethane;	Trifluoromethanesulfonic anhydride (0.135 mL, 0.80 mmol) was added to a solution of ethyl (+-)-(E)-4-(4-(3,3-dimethylcyclohexan-1-on-2-yl)but-3-en-1-yn-1-yl)benzoate (93 mg, 0.30 mmol) and <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (165 mg, 0.80 mmol) in dichloromethane (4.5 mL). The flask was sealed with a plastic cap and the mixture was stirred for 3 days at room temperature. The solution was diluted with diethyl ether and washed with saturated NH4 Cl, 5percent aqueous NaHCO3, and brine, and dried (MgSO4). The solvents were removed under reduced pressure, and the residue was purified by silica gel chromatography (10:1, hexane:ethyl acetate) to give the title compounds as a 1:1 mixture of isomers. The compounds were separated by HPLC using a Whatman Partisil-10 1*50 cm column (95:5, hexane:ethyl acetate) to provide ethyl (E)-4-(4-(1-(trifluromethanesulfonyl)oxy-3,3-dimethylcyclohexen-2-yl)but-3-en-1-yn-1-yl)benzoate: PNMR (300 MHz, CDCl3) delta 1.16 (s, 6 H), 1.39 (t, 3 H, J=7.1 Hz), 1.53 (m, 2 H), 1.79 (m, 2 H), 2.44 (m, 2 H), 4.37 (q, 2 H, J=7.1 Hz), 6.08 (d, 1 H, J=16.5 Hz), 6.52 (d, 1 H, J=16.5 Hz), 7.50 (d, 2 H, J=8.4 Hz), 7.99 (dd, 2 H, J=2.0, 8.4 Hz), and ethyl (+-)-(E)-4-(4-(2-(trifluromethanesulfonyl)oxy-4,4-dimethylcyclohexen-3-yl)but-3-en-1-yn-1-yl)benzoate: PNMR (300 MHz, CDCl3) delta 0.95 (s, 3H), 1.04 (s, 3 H), 1.25-1.58 (m, 4 H), 1.39 (t, 3 H, J =7.2 Hz), 2.23 (m, 2 H), 2.76 (d, 1 H, J=11.3 Hz), 4.37 (q, 2 H, J=7.2 Hz), 5.82 (d, 1 H, J=14.5 Hz), 5.86 (t, 1 H, J=4.5 Hz), 6.08 (dd, 1 H, J=11.3, 14.5 Hz), 7.48 (d, 2 H, J=8.3 Hz), 7.98 (d, 2 H, J=8.3 Hz).

Reference： [1]Patent: US5760276,1998,A

84
[ 38222-83-2 ]
[ 158952-20-6 ]
6α,9α-difluoro-11β-hydroxy-16α,17α-isopropylidenedioxy-17β-(fluoromethylthio)androsta-1,4-dien-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With xenon difluoride;molecular sieve; In dichloromethane; water; ethyl acetate;	3.1 6alpha,9alpha-Difluoro-11beta-hydroxy-16alpha,17alpha-isopropylidenedioxy-17beta-(fluoromethylthio)androsta-1,4-dien-3-one A mixture of 6alpha,9alpha-difluoro-11beta-hydroxy-16alpha,17alpha-isopropylidenedioxy-17beta-methylthio-androsta-1,4-dien-3-one (5.06 g, 11.5 mmol), 2,6-di-t-butyl-4-methylpyridine (5.19 g, 25.3 mmol) and activated molecular sieve (type 4 A, 7.5 g) in dry dichloromethane (250 ml) is stirred for 1.5 hours under an argon atmosphere at 20° C. Xenon difluoride (2.15 g, 12.7 mmol) is added in one portion and the mixture stirred at 20° C. for 3 hours. After the molecular sieve is filtered off, the homogeneous solution is poured into ice cold water (500 ml), decanted and the aqueous phase extracted with dichloromethane (200 ml). The combined organic phases are washed with brine (100 ml) and concentrated in vacuo. The residue is taken up in ethyl acetate (500 ml), washed with hydrochloric acid (1N, three times 250 ml), water (250 ml), brine (250 ml) and then the organic phase is dried over magnesium sulfate. Filtration of the dessicant and concentration in vacuo gives a white solid (3.6 g) which is purified by preparative HPLC using a Dynamax RP-18 column and methanol/water as mobile phase. 6alpha,9alpha-difluoro-11beta-hydroxy-16alpha,17alpha-isopropylidenedioxy-17beta-(fluoromethylthio)androsta-1,4-dien-3-one (2.4 g, 5.23 mmol) is obtained as a white solid which is recrystallized from acetonitrile, m.p. 268°-9° C.; [a]26 =+162°, c=0.057 (CH3CN); N.M.R. (DMSO, d6): 1.06 (s, 3H), 1.36 (s, 3H), 1.45 (s, 3H), 1.46-1.57 (m, 2H), 1.50 (s, 3H), 1.69 (dt, 1H), 1.73 (d, 1H), 1.82 (dt, 1H), 2.05 (dt, 1H), 2.29 (c, 1H), 2.47-2.63 (m, 1H), 4.15 (c, 1H), 4.63 (d, 1H), 5.52 (c, 1H), 5.62 (m, 1H), 5.65 (dd, 1H), 5.79 (dd, 1H), 6.10 (s, 1H), 6.29 (dd, 1H), 7.25 (dd, 1H); Found: C, 60.2; H, 6.37percent Calculated for C23 H29 F3 O4 S: C, 60.25; H,[6.37percent].

Reference： [1]Patent: US5801165,1998,A

85
[ 38222-83-2 ]
[ 172786-94-6 ]
[ 119170-14-8 ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoromethanesulfonic acid anhydride; In dichloromethane;	(i) Androst-3,5,16-triene-17-(trifluoromethylsulfonate)-3-carboxylic acid To a solution of androst-3,5-diene-17-one-3-carboxylic acid (315 mg, 1 mmol), prepared as in Example 14, in 10 ml methylene chloride is added 2,6-di-t-butyl-4-methylpyridine (272 mg, 1.5 mmol) and trifluoromethanesulfonic anhydride (0.3 ml, 1.6 mmol) and the solution is stirred for 4 hours. The reaction mixture is then diluted with methylene chloride, washed with 10percent hydrochloric acid, brine, and concentrated to yield crude andros-3,5,16-triene-17-(trifluoromethylsulfonate)-3-carboxylic acid.
	With trifluoromethanesulfonic acid anhydride; In dichloromethane;	(i) Androst-3,5,16-triene-17-(trifluoromethylsulfonate)-3-carboxylic acid To a solution of androst-3,5-diene-17-one-3-carboxylic acid (314 mg, 1 mmol), prepared as in Example 12, in 10 ml methylene chloride is added 2,6-di-t-butyl-4-methylpyridine (272 mg, 1.5 mmol) and trifluoromethanesulfonic anhydride (0.3 ml, 1.6 mmol) and the solution is stirred for 4 hours. The reaction mixture is then diluted with methylene chloride, washed with 10percent hydrochloric acid, brine, and concentrated to yield crude androst-3,5,16-triene-17-(trifluoromethylsulfonate)-3-carboxylic acid.
	With trifluoromethanesulfonic acid anhydride; In dichloromethane;	(i) Androst-3,5,16-triene-17-(trifluoromethylsulfonate)-3-carboxylic acid To a solution of androst-3,5-diene-17-one-3-carboxylic acid (314 mg, 1 mmol), prepared as in Example 14, in 10 ml methylene chloride is added 2,6-di-t-butyl-4-methylpyridine (272 mg, 1.5 mmol) and trifluoromethanesulfonic anhydride (0.3 ml, 1.6 mmol) and the solution is stirred for 4 hours. The reaction mixture is then diluted with methylene chloride, washed with 10percent hydrochloric acid, brine, and concentrated to yield crude androst-3,5,16-triene-17-(trifluoromethylsulfonate)-3-carboxylic acid.

Reference： [1]Patent: US4910226,1990,A
[2]Patent: US5017568,1991,A
[3]Patent: EP289327,1991,B1

86
[ 38222-83-2 ]
androst-3,5-diene-17-one-3-phosphonic acid [ No CAS ]
Androst-3,5,16-triene-17-(trifluoromethyl-sulfonate)-3-phosphonic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoromethanesulfonic acid anhydride; In dichloromethane;	(i) Androst-3,5,16-triene-17-(trifluoromethyl-sulfonate)-3-phosphonic acid To a solution of androst-3,5-diene-17-one-3-phosphonic acid (314 mg, 1 mmol), prepared as in Example 14, in 10 ml methylene chloride is added 2,6-di-t-butyl-4-methylpyridine (272 mg, 1.5 mmol) and trifluoromethanesulfonic anhydride (0.3 ml, 1.6 mmol) and the solution is stirred for 4 hours. The reaction mixture is then diluted with methylene chloride, washed with 10percent hydrochloric acid, brine, and concentrated to yield crude androst-3,5,16-triene-17-(trifluoromethylsulfonate)-3-phosphonic acid.

Reference： [1]Patent: US4946834,1990,A

87
[ 38222-83-2 ]
androst-3,5-diene-17-one-3-phosphinic acid [ No CAS ]
androst-3,5,16-triene-17-(trifluoromethylsulfonate)-3-phosphinic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoromethanesulfonic acid anhydride; In dichloromethane;	(i) Androst-3,5,16-triene-17-(trifluoromethylsulfonate)-3-phosphinic acid To a solution of androst-3,5-diene-17-one-3-phosphinic acid (320 mg), prepared as in Example 13, in 10 ml methylene chloride is added 2,6-di-t-butyl-4-methylpyridine (272 mg) and trifluoromethanesulfonic anhydride (0.3 ml) and the solution is stirred for 4 hours. The reaction mixture is then diluted with methylene chloride, washed with 10percent hydrochloric acid, brine, and concentrated to yield crude androst-3,5,16-triene-17-(trifluoromethyl-sulfonate)-3-phosphinic acid.

Reference： [1]Patent: US5026882,1991,A

88
[ 4530-20-5 ]
[ 38222-83-2 ]
[ 148777-88-2 ]

Yield	Reaction Conditions	Operation in experiment
46%	With trifluoromethanesulfonic acid anhydride; N-ethyl-N,N-diisopropylamine; In dichloromethane; ethyl acetate;	a) Preparation of 2-(2-maleimidoethoxy)ethanol above (2.70 mmoles) was added 10 mL of methylene chloride, and the solution cooled to 0°. To the solution was added 1.11 g of 2,6-di-tertbutyl-4-methylpyridine (2.70 mmoles, 100 molpercent) followed by 0.45 mL of trifluoromethanesulfonic anhydride (2.70 mmoles, 100 molpercent). The heterogeneous mixture was stirred at 0° for 1 h. The solution was filtered, and to the filtrate was added a solution of 0.47 g of N-tBOC-glycine (2.70 mmoles, 100 molpercent) and 0.47 mL of diisopropylethylamine (2.70 mmoles, 100 molpercent) in 10 mL of CH2 Cl2. The mixture was stirred for 2 h at room temperature. Ethyl acetate (100 mL) was added and the solution extracted with water (1*50 mL) then dried over Na2S04. Filtration and removal of solvent gave an oil which was purified by flash chromatography on 100 mL of silica gel. The column was eluted with 400 mL of EtOAc/hexanes 1:1, giving 0.43 g of pure material (1.26 mmoles, 46percent). NMR (300 MHz, CDCl3) delta1.45 (s, 9H), 3.66 (m, 6H) 3.94(d, 2H), 4.26 (t, 2H), 5.14 (m, 1H), 6.74 (s, 2H).

Reference： [1]Patent: US5144043,1992,A

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CAS No. :	38222-83-2	MDL No. :	MFCD00006305
Formula :	C₁₄H₂₃N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HVHZEKKZMFRULH-UHFFFAOYSA-N
M.W :	205.34	Pubchem ID :	98898
Synonyms :		Chemical Name :	2,6-Di-Tert-butyl-4-methylpyridine

Num. heavy atoms :	15
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.64
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	67.74
TPSA :	12.89 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.27 cm/s

Log Po/w (iLOGP) :	3.29
Log Po/w (XLOGP3) :	4.63
Log Po/w (WLOGP) :	3.99
Log Po/w (MLOGP) :	3.21
Log Po/w (SILICOS-IT) :	4.25
Consensus Log Po/w :	3.87

[ CAS No. 38222-83-2 ] {[proInfo.proName]}

Quality Control of [ 38222-83-2 ]

Related Doc. of [ 38222-83-2 ]

Product Details of [ 38222-83-2 ]

Calculated chemistry of [ 38222-83-2 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 38222-83-2 ]

Application In Synthesis of [ 38222-83-2 ]

[ 38222-83-2 ] Synthesis Path-Upstream 1~4

[ 38222-83-2 ] Synthesis Path-Downstream 1~88

Pharmaceutical Intermediates of
[ 38222-83-2 ]

Fosaprepitant Related Intermediates

Related Parent Nucleus of
[ 38222-83-2 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Log S (ESOL) :	-4.19
Solubility :	0.0131 mg/ml ; 0.000064 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.63
Solubility :	0.00485 mg/ml ; 0.0000236 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-4.84
Solubility :	0.00298 mg/ml ; 0.0000145 mol/l
Class :	Moderately soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.93

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 38222-83-2 ] {[proInfo.proName]}

Quality Control of [ 38222-83-2 ]

Related Doc. of [ 38222-83-2 ]

Product Details of [ 38222-83-2 ]

Calculated chemistry of [ 38222-83-2 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 38222-83-2 ]

Application In Synthesis of [ 38222-83-2 ]

[ 38222-83-2 ] Synthesis Path-Upstream 1~4

[ 38222-83-2 ] Synthesis Path-Downstream 1~88

Pharmaceutical Intermediates of [ 38222-83-2 ]

Fosaprepitant Related Intermediates

Related Parent Nucleus of [ 38222-83-2 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Pharmaceutical Intermediates of
[ 38222-83-2 ]

Related Parent Nucleus of
[ 38222-83-2 ]