Name: 21193-75-9|(2R,3R,4R)-2-(Hydroxymethyl)-3,4-dihydro-2H-pyran-3,4-diol|95%
Brand: Ambeed
SKU: A109730
Price: 26.0 USD
Availability: InStock
Rating: 95 (30 reviews)

1
[ 108-05-4 ]
[ 21193-75-9 ]
1-O-acetyl-2,6-anhydro-5-deoxy-D-arabino-hex-5-enitol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With 4 A molecular sieve; Lipase from Candida cylindracea (Lipase S-VII) In water for 0.75h; Ambient temperature;
91%	In N,N-dimethyl-formamide Subtilisin BPN', piperazine-N,N'-bis(2-ethanesulfonic acid) (PIPES)/ethylenediaminetetraacetic acid (EDTA), NAOAc buffer (pH 6.5);
84%	With lipase from Candida cylidracea (type VII) In water

84%	With Candida cylindracea lipase In water at 20℃; for 0.75h; Molecular sieve; Enzymatic reaction;
	In hexane; water; ethyl acetate	4 4. 4. Preparation of 6-O-acetylgalactal 1.0 g (6.85 mmol) of galactal is dissolved in about 1 ml of water, and 1-4 g of crushed molecular sieves, 25-75 ml of vinyl acetate and 800 mg of lipase from Candida cylindracea (Sigma) are added. The mixture is stirred at room temperature for about 45 min. Drying, filtration, concentration in vacuo and chromatography on silica gel (ethyl acetate/hexane 1:1) or crystallization (from ethyl acetate/hexane) yields 1.090 to 1.160 (85-90%) of the desired 6-O-acetylgalactal.

Reference： [1]Holla, E. Wolfgang [Angewandte Chemie, 1989, vol. 101, # 2, p. 222 - 223]
[2]Look, Gary C.; Ichikawa, Yoshitaka; Shen, Gwo-Jenn; Cheng, Pi-Wan; Wong, Chi-Huey [Journal of Organic Chemistry, 1993, vol. 58, # 16, p. 4326 - 4330]
[3]Bay, Sylvie; Berthier-Vergnes, Odile; Cantacuzene, Daniele [Carbohydrate Research, 1997, vol. 298, # 3, p. 153 - 161]
[4]Sunasee, Rajesh; Clive, Derrick L. J. [Chemical Communications, 2010, vol. 46, # 5, p. 701 - 703]
[5]Current Patent Assignee: SANOFI - US5496930, 1996, A

2
[ 108-05-4 ]
[ 21193-75-9 ]
[ 118396-86-4 ]

Yield	Reaction Conditions	Operation in experiment
75%	With lipase from Pseudomonas fluorescens; 4 A molecular sieve In water for 20h; Ambient temperature;
	In water	7 6. 7. Preparation of 3,6-di-O-acetylgatactal 1.0 g (6.85 mmol) of galactal is dissolved in about 1 ml of water, 1-4 g of crushed molecular sieves, 25-75 ml of vinyl acetate and 1.0 g of lipase from Pseudomonas spec. (Amano) are added and the mixture is stirred at room temperature overnight, Drying, filtration and chromatography on silica gel (ethyl acetate/hexane 2:3, v:v) result in 1.1 to 1.26 g (70-80%) of 3,6-di-O-acetylgalactal.

Reference： [1]Holla, E. Wolfgang [Angewandte Chemie, 1989, vol. 101, # 2, p. 222 - 223]
[2]Current Patent Assignee: SANOFI - US5496930, 1996, A

3
[ 108-24-7 ]
[ 21193-75-9 ]
[ 105581-69-9 ]

Yield	Reaction Conditions	Operation in experiment
83%	Stage #1: D-galactal With nitrobenzene In acetonitrile at 80℃; for 24h; Stage #2: acetic anhydride With pyridine In acetonitrile at 20℃;
	With pyridine Yield given;

Reference： [1]Tanaka, Takanori; Kawabata, Hirotoshi; Hayashi, Masahiko [Tetrahedron Letters, 2005, vol. 46, # 30, p. 4989 - 4991]
[2]Czernecki, S.; Vijayakumaran, K.; Ville, G. [Journal of Organic Chemistry, 1986, vol. 51, # 26, p. 5472 - 5475]

4
[ 100-39-0 ]
[ 21193-75-9 ]
[ 80040-79-5 ]

Yield	Reaction Conditions	Operation in experiment
92.3%		General procedure: To a solution of d-glucal (1.46g, 10mmol) in dry THF (20ml) was added NaH (1.44g, 60wt% dispersion in mineral oil, 36mmol) and tetrabutylammonium iodide (TBAI) at room temperature. The suspension was stirred for 30min then cooled in an ice-bath. Benzyl bromide (4.4ml, 36mmol) was added dropwise over a 5-min period, and after 10min the ice bath was removed. The reaction mixture was stirred overnight. Then 10ml of methanol was added slowly to dispose the excess NaH. The solvents were removed under reduced pressure at 35C. The residue was then dissolved in 200ml of dichloromethane (DCM) and washed with water and brine respectively. Then the mixture was dried over anhydrous MgSO4. Removal of MgSO4 was carried on, and the filtrate was evaporated to give a yellow oil, which solidified to a yellow solid after submitted to high vacuum overnight. Further purification by column chromatography (silica gel, EtOAc/Petroleum ether=1:20, V:V) gave 1-3S as a colorless semisolid (4.05g, 98.8%).
62%		A solution of D-galactal (2.00 g, 13.7 mmol) in DMF (80 mL) was cooled to 0 C, then treated with sodium hydride (2.13 g, 53.2 mmol). The solution was stirred at 0 C for 30 minutes, then treated with benzyl bromide (5.6 mL, 47 mmol) and allowed to warm to room temperature. After 19 hours, 8the solution was diluted with water (40 mL) and the product extracted with diethyl ether (3 x 100mL). The organic fractions were combined, dried, filtered and concentrated to provide the crude product as a concentrated solution in DMF. Purification by column chromatography (9:1hexanes:ethyl acetate) afforded 5 (3.53 g, 62%) as a white solid. The spectral data matched those reported previously.4

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 4613 - 4615
[2]Bulletin of the Chemical Society of Japan,1999,vol. 72,p. 765 - 777
[3]Journal of the American Chemical Society,2012,vol. 134,p. 1978 - 1981
[4]Organic and biomolecular chemistry,2020,vol. 18,p. 1165 - 1184
[5]Journal of the American Chemical Society,2019,vol. 141,p. 12939 - 12945
[6]European Journal of Medicinal Chemistry,2014,vol. 77,p. 211 - 222
[7]European Journal of Organic Chemistry,2005,p. 3279 - 3285
[8]European Journal of Organic Chemistry,2005,p. 2671 - 2676
[9]European Journal of Organic Chemistry,2004,p. 468 - 473
[10]Journal of Organic Chemistry,1994,vol. 59,p. 8256 - 8260
[11]Green Chemistry,2015,vol. 17,p. 2545 - 2551
[12]Journal of Organic Chemistry,2008,vol. 73,p. 7775 - 7778
[13]Carbohydrate Research,1981,vol. 98,p. 25 - 36
[14]Organic Letters,2012,vol. 14,p. 174 - 177
[15]Tetrahedron,2014,vol. 70,p. 7032 - 7043
[16]Journal of Organic Chemistry,2016,vol. 81,p. 11394 - 11396
[17]Organic Letters,2009,vol. 11,p. 939 - 942
[18]Chemistry - A European Journal,2012,vol. 18,p. 8208 - 8215
[19]Organic Letters,2015,vol. 17,p. 5698 - 5701

5
[ 98-88-4 ]
[ 21193-75-9 ]
[ 130323-36-3 ]

Yield	Reaction Conditions	Operation in experiment
76%	With pyridine; methanol In 1,2-dichloro-ethane 1) 45 min, 0 deg C, 2) 30 min, room temperature;
	With pyridine at 0℃; for 1.5h; regioselective reaction;

Reference： [1]Jacquinet [Carbohydrate research, 1990, vol. 199, # 2, p. 153 - 181]
[2]Location in patent: scheme or table Zhong, Ming; Meng, Xiang-Bao; Li, Zhong-Jun [Carbohydrate Research, 2010, vol. 345, # 9, p. 1099 - 1106]

6
[ 107-30-2 ]
[ 21193-75-9 ]
1,5-anhydro-3,4,6-tri-O-methoxymethyl-D-lyxo-hex-1-enitol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; Inert atmosphere;
	With N-ethyl-N,N-diisopropylamine In dichloromethane for 48h; 0 deg C -> R.T.; Yield given;

Reference： [1]Balmond, Edward I.; Coe, Diane M.; Galan, M. Carmen; McGarrigle, Eoghan M. [Angewandte Chemie - International Edition, 2012, vol. 51, # 36, p. 9152 - 9155]
[2]Lafont, Dominique; Descotes, Gerard [Carbohydrate Research, 1987, vol. 166, p. 195 - 210]

7
[ 18162-48-6 ]
[ 21193-75-9 ]
[ 124751-19-5 ]

Yield	Reaction Conditions	Operation in experiment
77%	With 1H-imidazole In N,N-dimethyl-formamide; toluene at 0 - 25℃; for 12h; Inert atmosphere;
76%	With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere;
73%	With pyridine 1) 0 deg C, 1 h, 2) RT, 15 h;

72%	With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 10h; Inert atmosphere;
70%	With 1H-imidazole In N,N-dimethyl-formamide Ambient temperature;
68%	With pyridine; dmap In N,N-dimethyl-formamide at 0 - 20℃;
	With pyridine at 0℃;
	With 3 A molecular sieve; di(n-butyl)tin oxide 1) CH₃CN, reflux, 150 min; 2) CH₃CN, 1 h, room temperature; Yield given. Multistep reaction;
	With 1H-imidazole In N,N-dimethyl-formamide for 16h;
10.78 g	With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 12h;
	With 1H-imidazole In N,N-dimethyl-formamide at 20℃;
	With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;

Reference： [1]Keith, D. Jamin; Townsend, Steven D. [Journal of the American Chemical Society, 2019, vol. 141, # 32, p. 12939 - 12945]
[2]Kim, Yongju; Oh, Keunhee; Song, Heebum; Lee, Dong-Sup; Park, Seung Bum [Journal of Medicinal Chemistry, 2013, vol. 56, # 17, p. 7100 - 7109]
[3]Kozilowski; Lee [Journal of Organic Chemistry, 1990, vol. 55, # 3, p. 863 - 870]
[4]Dai, Yuanwei; Zheng, Jianfeng; Zhang, Qiang [Organic Letters, 2018, vol. 20, # 13, p. 3923 - 3927]
[5]Danishefsky, Samuel J.; Gervay, Jacquelyn; Peterson, John M.; McDonald, Frank E.; Koseki, Koshi; Griffith, David A.; Oriyama, Takeshi; Marsden, Stephen P. [Journal of the American Chemical Society, 1995, vol. 117, # 7, p. 1940 - 1953]
[6]Baba, Takayuki; Huang, Guobin; Isobe, Minoru [Tetrahedron, 2003, vol. 59, # 35, p. 6851 - 6872]
[7]Mereyala, Hari Babu; Venkataramanaiah, Kanamarlapudi C [Journal of Chemical Research, Miniprint, 1991, # 8, p. 1953 - 1966]
[8]Leteux, Christine; Veyrieres, Alain [Journal of the Chemical Society. Perkin transactions I, 1994, # 18, p. 2647 - 2656]
[9]Kirschning, Andreas [Journal of Organic Chemistry, 1995, vol. 60, # 5, p. 1228 - 1232]
[10]Aurrecoechea, José M.; Arrate, Mónica; Gil, Jesús H.; López, Beatriz [Tetrahedron, 2003, vol. 59, # 29, p. 5515 - 5522]
[11]Aurrecoechea, José M.; Gil, Jesús H.; López, Beatriz [Tetrahedron, 2003, vol. 59, # 36, p. 7111 - 7121]
[12]Mabit, Thibaud; Siard, Aymeric; Legros, Frédéric; Guillarme, Stéphane; Martel, Arnaud; Lebreton, Jacques; Carreaux, François; Dujardin, Gilles; Collet, Sylvain [Chemistry - A European Journal, 2018, vol. 24, # 53, p. 14069 - 14074]

8
[ 18162-48-6 ]
[ 21193-75-9 ]
[ 121702-69-0 ]

Yield	Reaction Conditions	Operation in experiment
87%	With 1H-imidazole In N,N-dimethyl-formamide at 55℃; for 48h;
86%	With 1H-imidazole In N,N-dimethyl-formamide at 60℃; for 48h;
86%	With 1H-imidazole In N,N-dimethyl-formamide at 60℃; for 48h;

84%	With 1H-imidazole; dmap In N,N-dimethyl-formamide 1.) 60 deg C, 20 h, 2.) 25 deg C, 36 h;
73%	With 1H-imidazole; dmap In N,N-dimethyl-formamide at 60℃; for 36h; Inert atmosphere;
	With 1H-imidazole; dmap In N,N-dimethyl-formamide at 50℃; for 48h;

Reference： [1]Carell, Thomas; Ensfelder, Timm T.; Heiss, Matthias; Hillmeier, Markus; Kellner, Stefanie; Müller, Markus; Michalakis, Stylianos; Schön, Alexander; Scheel, Constanze; Thumbs, Peter; Wagner, Mirko [Angewandte Chemie - International Edition, 2020, vol. 59, # 30, p. 12352 - 12356][Angew. Chem., 2020, vol. 132, # 30, p. 12451 - 12455,5]
[2]Crich, David; Ritchie, Timothy J. [Journal of the Chemical Society. Perkin transactions I, 1990, # 4, p. 945 - 954]
[3]Crich, David; Ritchie, Timothy [Carbohydrate Research, 1989, vol. 190, p. C3 - C6]
[4]Berlin, William K.; Zhang, Wen-Sheng; Shen, T. Y. [Tetrahedron, 1991, vol. 47, # 1, p. 1 - 20]
[5]Balmond, Edward I.; Coe, Diane M.; Galan, M. Carmen; McGarrigle, Eoghan M. [Angewandte Chemie - International Edition, 2012, vol. 51, # 36, p. 9152 - 9155]
[6]Location in patent: experimental part Li, Hou-Hua; Ye, Xin-Shan [Organic and Biomolecular Chemistry, 2009, vol. 7, # 18, p. 3855 - 3861]

9
[ 18162-48-6 ]
[ 21193-75-9 ]
[ 121702-69-0 ]
[ 111902-03-5 ]

Yield	Reaction Conditions	Operation in experiment
83%	With 1H-imidazole In N,N-dimethyl-formamide Ambient temperature; Yield given;
83%	With 1H-imidazole In N,N-dimethyl-formamide Ambient temperature; Yields of byproduct given;

Reference： [1]Kinzy, Willy; Schmidt, Richard R. [Tetrahedron Letters, 1987, vol. 28, # 18, p. 1981 - 1984]
[2]Kinzy, Willy; Schmidt, Richard R. [Tetrahedron Letters, 1987, vol. 28, # 18, p. 1981 - 1984]

10
[ 18162-48-6 ]
[ 21193-75-9 ]
[ 111902-03-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	With 1H-imidazole In N,N-dimethyl-formamide at 0℃; for 0.75h;
56%	With pyridine; tetrabutylammomium bromide at 50℃; for 5h; regioselective reaction;	Regioselective double silylation of monosaccharide polyols or silylation of secondary carbinols: General procedure: To a mixture of the polyol substrate (0.5-1 mmol), TBAB and the silylating agent, pyridine was added under air (see Table 3 for stoichiometric proportions). The mixture was kept under stirring at 50 °C. Upon completion of the reaction (1-6 hours), the mixture was concentrated under vacuum and then submitted to silica-gel flash chromatography (eluents: hexane/ethyl acetate mixtures) to afford the di-O-silylated products in the yields indicated in Table 3. The regiochemistry of the double silylation was determined by acetylation of the isolated products (2:1v/v pyridine/acetic anhydride, overnight, rt) and subsequent NMR analysis.
	With 1H-imidazole In N,N-dimethyl-formamide for 16h;

Reference： [1]Jacquinet [Carbohydrate research, 1990, vol. 199, # 2, p. 153 - 181]
[2]Traboni, Serena; Bedini, Emiliano; Iadonisi, Alfonso [Beilstein Journal of Organic Chemistry, 2016, vol. 12, p. 2748 - 2756]
[3]Kirschning, Andreas [Journal of Organic Chemistry, 1995, vol. 60, # 5, p. 1228 - 1232]

11
[ 79-04-9 ]
[ 21193-75-9 ]
[ 132562-87-9 ]

Yield	Reaction Conditions	Operation in experiment
95%	With pyridine In acetonitrile at 0℃; for 0.75h;

Reference： [1]Bouhroum, Salah; Vottero, Philippe J. A. [Tetrahedron Letters, 1990, vol. 31, # 51, p. 7441 - 7444]

12
[ 58479-61-1 ]
[ 21193-75-9 ]
1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-lyxo-hex-1-enitol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With triethylamine In N,N-dimethyl-formamide for 3h; Ambient temperature;
82%	With 1H-imidazole In tetrahydrofuran 1) 0 deg C, 1 h, 2) rt, 4 h;
80%	With dmap; triethylamine In N,N-dimethyl-formamide at 0 - 20℃;

72%	With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 10h; Inert atmosphere;
72%	With 1H-imidazole In N,N-dimethyl-formamide at 0℃; for 12h; Inert atmosphere;	Compound S1 (2g, 13.7mmol) was dissolved in 30mL DMF, imidazole (1.8639g, 27.4mmol, 2eq) was added, TBDPSCl (4mL, 15.1mmol, 1.1eq) was added at 0°C, and the reaction was carried out under N2 protection for 12h. The reaction system was poured into ice water and stirred and quenched, extracted with ethyl acetate, washed with saturated brine, dried with anhydrous Na2SO4, filtered with suction, spin-dried the solvent, and passed through the column with (PE:EA=10:1-5:1) to obtain S10 Oily liquid, (3.7927g, 72%).
	With 1H-imidazole In N,N-dimethyl-formamide Ambient temperature;
	With pyridine; dmap
5.2 g	With 1H-imidazole In N,N-dimethyl-formamide at 20℃; Cooling with ice;	5 (5) The crude product compound d (2.7 g, 18.5 mmol) obtained in the previous step was dissolved in a round bottom flask (100 ml) using dry N,N-dimethylformamide (18 ml) as solvent. The imidazole (1.8 g, 27.0 mmol) activated by vacuum filtration at 50 ° C for 0.5 h was added as a catalyst and tert-butyl diphenyl chlorosilane under ice-cooling conditions. (4.3 ml, 16.5 mmol) After a period of reaction, the mixture was gradually warmed to room temperature for 1 h, and the reaction was judged by thin layer chromatography (petroleum ether: ethyl acetate = 6:1). After the reaction, methanol (1.5 ml) was added to the system to terminate the reaction. The excess solvent was removed by distillation under reduced pressure (-0.09 MPa, 45 ° C), and the mixture was diluted with dichloromethane, washed three times with water and then washed with saturated brine. Drying with sodium sulfate, The excess solvent was removed by vacuum distillation (-0.09 MPa, 45 ° C) to give the crude product as a pale yellow powder, which was purified by silica gel column chromatography ( petroleum ether: ethyl acetate = 8:1) to give compound e (5.2 g) , 13 mmol), the yield was 91.2%.

Reference： [1]Gervay, Jacquelyn; Peterson, John M.; Oriyama, Takeshi; Danishefsky, Samuel J. [Journal of Organic Chemistry, 1993, vol. 58, # 20, p. 5465 - 5468]
[2]Alonso, R. A.; Vite, G. D.; McDevitt, R. E.; Fraser-Reid, B. [Journal of Organic Chemistry, 1992, vol. 57, # 2, p. 573 - 584]
[3]Cheshev; Kononov; Tsvetkov; Shashkov; Nifantiev [Russian Journal of Bioorganic Chemistry, 2002, vol. 28, # 5, p. 419 - 429]
[4]Dai, Yuanwei; Zheng, Jianfeng; Zhang, Qiang [Organic Letters, 2018, vol. 20, # 13, p. 3923 - 3927]
[5]Current Patent Assignee: JIANGXI NORMAL UNIVERSITY - CN113200951, 2021, A Location in patent: Paragraph 0063-0064
[6]Shekhani, Mohammed Saleh; Khan, Khalid Mohammed; Mahmood, Khalid; Shah, Pir Mozzam; Malik, Sohail [Tetrahedron Letters, 1990, vol. 31, # 12, p. 1669 - 1670]
[7]Danishefsky, Samuel J.; Gervay, Jacquelyn; Peterson, John M.; McDonald, Frank E.; Koseki, Koshi; Griffith, David A.; Oriyama, Takeshi; Marsden, Stephen P. [Journal of the American Chemical Society, 1995, vol. 117, # 7, p. 1940 - 1953]
[8]Current Patent Assignee: SICHUAN UNIVERSITY OF SCIENCE AND ENGINEERING - CN109912642, 2019, A Location in patent: Paragraph 0031-0032; 0038

13
[ 21193-75-9 ]
[ 762-72-1 ]
[ 158780-35-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With trimethylsilyl trifluoromethanesulfonate In dichloromethane; acetonitrile at -78℃; for 1h;

Reference： [1]Toshima, Kazunobu; Ishizuka, Toru; Matsuo, Goh; Nakata, Masaya [Tetrahedron Letters, 1994, vol. 35, # 31, p. 5673 - 5676] Toshima, Kazunobu; Matsuo, Goh; Ishizuka, Toru; Ushiki, Yasunobu; Nakata, Masaya; Matsumura, Shuichi [Journal of Organic Chemistry, 1998, vol. 63, # 7, p. 2307 - 2313]

14
[ 21193-75-9 ]
[ 10226-85-4 ]

Yield	Reaction Conditions	Operation in experiment
85%	With dihydrogen peroxide; potassium bromide In water for 2h; chloroperoxidase, citric-phosphate buffer, pH 3;

Reference： [1]Liu, Kevin K.-C.; Wong, Chi-Huey [Journal of Organic Chemistry, 1992, vol. 57, # 13, p. 3748 - 3750]

15
[ 21193-75-9 ]
(3R,4S,5R,6R)-6-(hydroxymethyl)-3-iodotetrahydro-2H-pyran-2,4,5-triol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With dihydrogen peroxide; potassium iodide In water for 0.5h; chloroperoxidase, citric-phosphate buffer, pH 3;

Reference： [1]Liu, Kevin K.-C.; Wong, Chi-Huey [Journal of Organic Chemistry, 1992, vol. 57, # 13, p. 3748 - 3750]

16
[ 21193-75-9 ]
1,5-anhydro-2-deoxy-D-threo-hex-1-en-3-ulose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With ethene In N,N-dimethyl-formamide at 20℃; for 45h;
	With dipyridinium dichromate; acetic acid In ethyl acetate Ambient temperature;
	With ethene; palladium In N,N-dimethyl-formamide at 50℃; for 96h; Yield given;

Reference： [1]Hayashi, Masahiko; Yamada, Kanako; Arikita, Osamu [Tetrahedron, 1999, vol. 55, # 28, p. 8331 - 8340]
[2]Czernecki, S.; Vijayakumaran, K.; Ville, G. [Journal of Organic Chemistry, 1986, vol. 51, # 26, p. 5472 - 5475]
[3]Hayashi; Yamada; Arikita [Tetrahedron Letters, 1999, vol. 40, # 6, p. 1171 - 1174]

17
[ 4098-06-0 ]
[ 21193-75-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium methoxide In methanol
99%	With lipase A from Aspergillus niger In aq. phosphate buffer; acetonitrile at 25℃; for 1h; Enzymatic reaction;
99%	With methanol; sodium methoxide at 20℃; for 0.5h;	3.1. General Procedure for the Synthesis of Glycals General procedure: A catalytic amount of MeONa (0.03 g, 0.57 mmol) was added to a solution of tri-O-acetyl-D-glycal (2.5 g, 9.18 mmol) in methanol (25 mL) and the resulting reaction mixture was stirred at rt. The progress of reactions was monitored by silica gel thin-layer chromatography plates. After 30 min, the solution was filtered on a Schott funnel over a resin layer (Amberlite IR120) and celite. Evaporation of the organic solvent afforded a pure product.

97%	With ammonia In methanol at 20℃; for 5h;
97.6%	With methanol; potassium carbonate
96%	With methanol; potassium permanganate; trimethyl-sulfonium iodide at 25℃; chemoselective reaction;
95%	With methanol; sodium methoxide at 20℃; Inert atmosphere;
95%	Stage #1: (2R,3R,4R)-2-(acetoxymethyl)-3,4-dihydro-2H-pyran-3,4-diyl diacetate With sodium methoxide In methanol at 25℃; for 2h; Inert atmosphere; Stage #2:
93%	With sodium methoxide In methanol at 20℃; for 2h;	6.6-3.1 Step 1: To a solution of (2R,3R,4R)-2-(acetoxymethyl)-3,4-dihydro-2H-pyran-3,4-diyl diacetate (A126-1, 30.0 g, 55.1 mmol) in MeOH (300 mL) was added NaOMe (31.0 mL,165.3 mmol, 5.4 M in MeOH) at room temperature. The mixture was stirred at room temperature for 2 hours. The reaction was neutralized by the addition of Amberlite IR 120 (H+) ion exchange resin. The solution was filtered through a glass fritted funnel with a pad of Celite to remove the resin. The filtrate was concentrated to dryness to give a crude triol. The crude material was passed through a plug of silica (70:30 to 85: 15 EtOAc/hexanes) to give D-galactal triol (A126-2,15.0 g 93%) as white solid. LC-MS (ESI) found: 147 [M+H]+.
93%	With sodium methoxide In methanol at 20℃; for 2h;	6.6-3.1 Step 1: To a solution of (2R,3R,4R)-2-(acetoxymethyl)-3,4-dihydro-2H-pyran-3,4-diyl diacetate (A126-1, 30.0 g, 55.1 mmol) in MeOH (300 mL) was added NaOMe (31.0 mL,165.3 mmol, 5.4 M in MeOH) at room temperature. The mixture was stirred at room temperature for 2 hours. The reaction was neutralized by the addition of Amberlite IR 120 (H+) ion exchange resin. The solution was filtered through a glass fritted funnel with a pad of Celite to remove the resin. The filtrate was concentrated to dryness to give a crude triol. The crude material was passed through a plug of silica (70:30 to 85: 15 EtOAc/hexanes) to give D-galactal triol (A126-2,15.0 g 93%) as white solid. LC-MS (ESI) found: 147 [M+H]+.
92%	With triethylamine In methanol; lithium hydroxide monohydrate at 20℃; for 24h;
92%	With lithium hydroxide monohydrate; triethylamine In methanol at 20℃;
89%	With methanol; natrium
87%	With sodium methoxide In methanol for 72h;
	With ammonia In methanol for 15h; Ambient temperature; Yield given;
	With sodium methoxide In methanol
	With natrium In methanol for 12h;
	With anion-exchange resin (Amberlite IRN-78, OH^- form) In methanol for 15h; Ambient temperature;
	With ammonia In methanol
0.73 g	With sodium methoxide In methanol at 20℃; for 24h;
	With sodium methoxide In methanol
	With methanol; sodium methoxide at 20℃; for 3h;
	With sodium methoxide In methanol at 20℃;
	With sodium methoxide In methanol at 20℃; for 1.5h;
	With sodium methoxide In methanol
	With methanol; sodium methoxide at 20℃; for 2h;
	With sodium methoxide In methanol at 20℃;
	With sodium methoxide In methanol at 20℃; for 24h; Inert atmosphere;
	With methanol; sodium methoxide at 0 - 20℃; for 1h; Inert atmosphere;
	With methanol; natrium at 20℃; for 0.166667h; Inert atmosphere;	D-Galactal Using a modification of Kozikowski’s procedure,1 a magnetically stirred solution of D-galactose (S2, 125 mg, 0.7 mmol) in acetic anhydride (75 mL, 790 mmol) was treated dropwise with conc. perchloric acid (0.45 mL, 6.9 mmol). The remaining D-galactose (19.9 g, 110.3 mmol) was slowly added over 30 minutes, at a rate that maintained a temperature of 40-50 °C. Upon complete addition of D-galactose, the solution was allowed to cool to room temperature, then treated with a 33% (w/w) solution of hydrobromic acid in acetic acid (75 mL, 410 mmol). After 90 minutes, the solution was diluted with dichloromethane (180 mL) and washed with ice-cold water (2 x 50 mL), then with cold saturated sodium bicarbonate solution (4 x 100 mL). The organic phase was dried, filtered and concentrated to afford crude tetra-O-acetyl-α-D-galactopyranosyl bromide as a pale-yellow oil.A mechanically stirred dispersion of zinc dust (48.0 g, 734 mmol) in water (150 mL) was cooled to 0 °C, diluted with acetic acid (150 mL), then treated dropwise over one hour with a solution of tetra-O-acetyl-α-D-galactopyranosyl bromide in diethyl ether (150 mL). The reaction was allowed to warm to room temperature and left to proceed overnight. The solution was filtered, then diluted with dichloromethane (200 mL). The solution was then washed successively with water (3 x 60 mL), saturated sodium bicarbonate solution (3 x 50 mL) and brine (60 mL). The organic phase was dried, filtered and concentrated to provide tri-O-acetyl-D-galactal (S5) (27.7 g) as a pale-yellow oil.A solution of triethylamine (110 mL, 780 mmol) in methanol (50% of an aqueous solution, 1100 mL) was treated with tri-O-acetyl-D-galactal (27.7 g) and stirred for 90 minutes. The mixture was concentrated to liberate crude D-galactal, contaminated with triethylamine. The crude mixture was successively treated with portions of methanol, then concentrated to remove the triethylamine. The oil was dissolved in methanol (15 mL), then diluted successively with acetone (100 mL) and diethyl ether (200 mL), which led to the precipitation of impurities. The solution was filtered and concentrated to afford D-galactal as a pale-brown solid (6.63 g, 41% crude yield), which was used without further purification.
	With potassium carbonate In methanol at 20℃; for 3h;
	With sodium methoxide In methanol at 0℃; for 3h;
	With methanol; sodium methoxide at 20℃; for 3h; Inert atmosphere;
2.7 g	With methanol; sodium methoxide at 20℃;	4 (4) The crude product compound c (5.5 g, 20.2 mmol) obtained in the previous step was placed in a round bottom flask (250 ml). Then, methanol (84.0 ml) was added thereto, and the mixture was stirred to dissolve, followed by the addition of sodium methoxide (0.55 g, 10.2 mmol), and reacted at room temperature for 1-2 h. The reaction is carried out under normal temperature conditions to remove the acetic acid group (Ac). The reaction is judged by thin layer chromatography (dichloromethane: methanol = 10:1). After the reaction is completed, acetic acid is added to adjust the pH to neutral or weakly alkaline, and the pressure is reduced. Distillation (-0.09 MPa, 45 ° C) to remove excess solvent and spin dry to obtain a crude product as a pale yellow syrup. Separation by silica gel column chromatography (dichloromethane: Methanol = 5:1) gave the important intermediate compound d (perhydroxy galactose) (2.7 g, 18.5 mmol), The yield was 77.1%.
	With sodium methoxide In methanol Inert atmosphere;
	With methanol; sodium methoxide at 20℃; for 1.5h; Inert atmosphere;
	With sodium methoxide In methanol at 0℃; for 3h;

Reference： [1]Czernecki, S.; Ayadi, E.; Randriamandimby, D. [Journal of Organic Chemistry, 1994, vol. 59, # 26, p. 8256 - 8260]
[2]Dunne, Anthony; Palomo, Jose M. [RSC Advances, 2016, vol. 6, # 92, p. 88974 - 88978]
[3]Leśniak, Stanisław; Malinowska, Martyna; Tracz, Aleksandra; Zawisza, Anna [Molecules, 2022, vol. 27, # 6]
[4]Mamidyala, Sreeman K.; Dutta, Sanjay; Chrunyk, Boris A.; Preville, Cathy; Wang, Hong; Withka, Jane M.; McColl, Alexander; Subashi, Timothy A.; Hawrylik, Steven J.; Griffor, Matthew C.; Kim, Sung; Pfefferkorn, Jeffrey A.; Price, David A.; Menhaji-Klotz, Elnaz; Mascitti, Vincent; Finn [Journal of the American Chemical Society, 2012, vol. 134, # 4, p. 1978 - 1981]
[5]Current Patent Assignee: JIANGXI NORMAL UNIVERSITY - CN113200951, 2021, A Location in patent: Paragraph 0056-0058
[6]Gurawa, Aakanksha; Kashyap, Sudhir; Kumar, Manoj [RSC Advances, 2021, vol. 11, # 31, p. 19310 - 19315]
[7]Vedachalam, Seenuvasan; Tan, Shi Min; Teo, Hui Ping; Cai, Shuting; Liu, Xue-Wei [Organic Letters, 2012, vol. 14, # 1, p. 174 - 177]
[8]Keith, D. Jamin; Townsend, Steven D. [Journal of the American Chemical Society, 2019, vol. 141, # 32, p. 12939 - 12945]
[9]Current Patent Assignee: AVILAR THERAPEUTICS - WO2022/35997, 2022, A1 Location in patent: Page/Page column 286-288
[10]Current Patent Assignee: AVILAR THERAPEUTICS - WO2022/35997, 2022, A1 Location in patent: Page/Page column 286-288
[11]Chatterjee, Nirbhik; Pandit, Palash; Halder, Samiran; Patra, Amarendra; Maiti, Dilip K. [Journal of Organic Chemistry, 2008, vol. 73, # 19, p. 7775 - 7778]
[12]Maiti, Dilip K.; Halder, Samiran; Pandit, Palash; Chatterjee, Nirbhik; De Joarder, Dripta; Pramanik, Nabyendu; Saima, Yasmin; Patra, Amarendra; Maiti, Prabir K. [Journal of Organic Chemistry, 2009, vol. 74, # 21, p. 8086 - 8097]
[13]Jacquinet [Carbohydrate research, 1990, vol. 199, # 2, p. 153 - 181]
[14]Baba, Takayuki; Huang, Guobin; Isobe, Minoru [Tetrahedron, 2003, vol. 59, # 35, p. 6851 - 6872]
[15]Kozilowski; Lee [Journal of Organic Chemistry, 1990, vol. 55, # 3, p. 863 - 870]
[16]Bovin, Nicolai V.; Zurabyan, Sergei E.; Khorlin, Anatoly Y. [Carbohydrate Research, 1981, vol. 98, p. 25 - 36]
[17]Lafont, Dominique; Descotes, Gerard [Carbohydrate Research, 1987, vol. 166, p. 195 - 210]
[18]Czernecki, S.; Vijayakumaran, K.; Ville, G. [Journal of Organic Chemistry, 1986, vol. 51, # 26, p. 5472 - 5475]
[19]Kwon, Ohyun; Danishefsky, Samuel J. [Journal of the American Chemical Society, 1998, vol. 120, # 7, p. 1588 - 1599]
[20]Costantino, Valeria; Fattorusso, Ernesto; Imperatore, Concetta; Mangoni, Alfonso [Tetrahedron, 2002, vol. 58, # 2, p. 369 - 375]
[21]Cheshev; Kononov; Tsvetkov; Shashkov; Nifantiev [Russian Journal of Bioorganic Chemistry, 2002, vol. 28, # 5, p. 419 - 429]
[22]Aurrecoechea, José M.; Arrate, Mónica; Gil, Jesús H.; López, Beatriz [Tetrahedron, 2003, vol. 59, # 29, p. 5515 - 5522]
[23]Aurrecoechea, José M.; Gil, Jesús H.; López, Beatriz [Tetrahedron, 2003, vol. 59, # 36, p. 7111 - 7121]
[24]Dubbaka, Srinivas Reddy; Steunenberg, Peter; Vogel, Pierre [Synlett, 2004, # 7, p. 1235 - 1238]
[25]Postema, Maarten H. D.; Piper, Jared L.; Betts, Russell L.; Valeriote, Frederick A.; Pietraszkewicz, Halina [Journal of Organic Chemistry, 2005, vol. 70, # 3, p. 829 - 836]
[26]Pilgrim, Wayne; Murphy, Paul V. [Organic Letters, 2009, vol. 11, # 4, p. 939 - 942]
[27]Location in patent: experimental part Li, Hou-Hua; Ye, Xin-Shan [Organic and Biomolecular Chemistry, 2009, vol. 7, # 18, p. 3855 - 3861]
[28]Chabre, Yoann M.; Giguere, Denis; Blanchard, Bertrand; Rodrigue, Jacques; Rocheleau, Sylvain; Neault, Mathieu; Rauthu, Subhash; Papadopoulos, Alex; Arnold, Alexandre A.; Imberty, Anne; Roy, Rene [Chemistry - A European Journal, 2011, vol. 17, # 23, p. 6545 - 6562]
[29]Durantie, Estelle; Bucher, Christoph; Gilmour, Ryan [Chemistry - A European Journal, 2012, vol. 18, # 26, p. 8208 - 8215]
[30]Moore, Peter W.; Schuster, Julia K.; Hewitt, Russell J.; Stone, M. Rhia L.; Teesdale-Spittle, Paul H.; Harvey, Joanne E. [Tetrahedron, 2014, vol. 70, # 39, p. 7032 - 7043]
[31]Shu, Penghua; Zeng, Jing; Tao, Jinyi; Zhao, Yueqi; Yao, Guangmin; Wan, Qian [Green Chemistry, 2015, vol. 17, # 4, p. 2545 - 2551]
[32]Wang, Bang; Xiong, De-Cai; Ye, Xin-Shan [Organic Letters, 2015, vol. 17, # 22, p. 5698 - 5701]
[33]Mabit, Thibaud; Siard, Aymeric; Legros, Frédéric; Guillarme, Stéphane; Martel, Arnaud; Lebreton, Jacques; Carreaux, François; Dujardin, Gilles; Collet, Sylvain [Chemistry - A European Journal, 2018, vol. 24, # 53, p. 14069 - 14074]
[34]Current Patent Assignee: SICHUAN UNIVERSITY OF SCIENCE AND ENGINEERING - CN109912642, 2019, A Location in patent: Paragraph 0031-0032; 0037
[35]Ahadi, Somayeh; Awan, Shahid I.; Werz, Daniel B. [Chemistry - A European Journal, 2020]
[36]Conti, Gabriele; Cramer, Jonathan; Ernst, Beat; Girardi, Benedetta; Jiang, Xiaohua; Kokot, Maja; Kroezen, Blijke S.; Luisoni, Enrico; Müller, Jennifer; Rabbani, Said; Ricklin, Daniel; Schwardt, Oliver [ChemMedChem, 2020, vol. 15, # 18, p. 1706 - 1719]
[37]Yu, Changyue; Liu, Yichu; Xie, Xiong; Hu, Shulei; Zhang, Shurui; Zeng, Mingjie; Zhang, Dan; Wang, Jiang; Liu, Hong [Advanced Synthesis and Catalysis, 2021, vol. 363, # 21, p. 4926 - 4931]

18
[ 824-94-2 ]
[ 21193-75-9 ]
[ 183730-71-4 ]

Yield	Reaction Conditions	Operation in experiment
70%	With tetrabutylammomium bromide; di(n-butyl)tin oxide In benzene
	With tetrabutylammomium bromide; di(n-butyl)tin oxide 1.) benzene, reflux, 2 h, 2.) benzene, reflux, 4 h; Yield given. Multistep reaction;

Reference： [1]Bilodeau, Mark T.; Park, Tae Kyo; Hu, Shuanghua; Randolph, John T.; Danishefsky, Samuel J.; Livingston, Philip O.; Zhang, Shengli [Journal of the American Chemical Society, 1995, vol. 117, # 29, p. 7840 - 7841]
[2]Park, Tae Kyo; Kim, In Jong; Hu, Shuanghua; Bilodeau, Mark T.; Randolph, John T.; Kwon, Ohyun; Danishefsky, Samuel J. [Journal of the American Chemical Society, 1996, vol. 118, # 46, p. 11488 - 11500]

19
[ 13154-24-0 ]
[ 21193-75-9 ]
[ 166021-01-8 ]

Yield	Reaction Conditions	Operation in experiment
82%	With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 16h;	14.14.4 Example 14.4: Synthesis of (2R,3R,4R)-2-(((triisopropylsilyl)oxy)methyl)-3,4-dihydro-2H- pyran-3,4-diol (168) A solution of (2R,3R,4R)-2-(hydroxymethyl)-3,4-dihydro-2H-pyran-3,4-diol (167, 10.00 g, 68.43 mmol, 1.00 equiv.) in DMF (100 mL) was cooled to 0°C and imidazole (9.32 g, 136.85 mmol, 2.00 equiv.) and TIPSCl (19.79 g, 102.64 mmol, 1.50 equiv.) were added. The reaction mixture was stirred for 16 h at r.t. EtOAc (500 mL) and water (500 mL) were added, the layers were separated, and the organic layer was washed with saturated aqueous NaCl- solution (100 mL), dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography (silica, 17% EtOAc in n-heptane) to yield (2R,3R,4R)-2- (((triisopropylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol (168, 17.00 g, 56.20 mmol, 82%) as a colorless oil. LC-MS (Method F): Rt[min] (UV-signal 214 nm): 2.11 M[g/mol]: 325 [M+Na+]
	With impramine In N,N-dimethyl-formamide Yield given;
1.2 g	With 1H-imidazole In N,N-dimethyl-formamide for 12h;

	With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃;
	With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;
	With 1H-imidazole In N,N-dimethyl-formamide at 0 - 4℃; for 6h; Inert atmosphere;
	With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 5h; Inert atmosphere;
	With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 1h; Inert atmosphere;

Reference： [1]Current Patent Assignee: SANOFI - WO2022/84331, 2022, A2 Location in patent: Paragraph 0446; 0449
[2]Kwon, Ohyun; Danishefsky, Samuel J. [Journal of the American Chemical Society, 1998, vol. 120, # 7, p. 1588 - 1599]
[3]Costantino, Valeria; Fattorusso, Ernesto; Imperatore, Concetta; Mangoni, Alfonso [Tetrahedron, 2002, vol. 58, # 2, p. 369 - 375]
[4]Location in patent: experimental part Otto, Frank; Doetz, Karl Heinz [Synthesis, 2008, # 14 SPEC. ISS., p. 2183 - 2190]
[5]Balmond, Edward I.; Coe, Diane M.; Galan, M. Carmen; McGarrigle, Eoghan M. [Angewandte Chemie - International Edition, 2012, vol. 51, # 36, p. 9152 - 9155]
[6]Parkan, Kamil; Pohl, Radek; Kotora, Martin [Chemistry - A European Journal, 2014, vol. 20, # 15, p. 4414 - 4419]
[7]Medina, Sandra; Harper, Matthew J.; Balmond, Edward I.; Miranda, Silvia; Crisenza, Giacomo E. M.; Coe, Diane M.; McGarrigle, Eoghan M.; Galan, M. Carmen [Organic Letters, 2016, vol. 18, # 17, p. 4222 - 4225]
[8]Dai, Yuanwei; Zheng, Jianfeng; Zhang, Qiang [Organic Letters, 2018, vol. 20, # 13, p. 3923 - 3927]

20
[ 100-39-0 ]
[ 21193-75-9 ]
[ 173008-15-6 ]

Yield	Reaction Conditions	Operation in experiment
80%	With dimethyltin dichloride; silver(l) oxide In acetonitrile at 20℃; for 24h; Inert atmosphere; regioselective reaction;
67%	With 2-Aminoethoxydiphenylborane; silver(l) oxide In acetonitrile at 40℃; for 16h; Inert atmosphere;
	With tetrabutylammomium bromide; bis(tri-n-butyltin)oxide 1.) benzene; Yield given. Multistep reaction;

With tetra-(n-butyl)ammonium iodide; bis(tri-n-butyltin)oxide In benzene at 90 - 110℃; Inert atmosphere;

Reference： [1]Saikam, Varma; Dara, Saidulu; Yadav, Mahipal; Singh, Parvinder Pal; Vishwakarma, Ram A. [Journal of Organic Chemistry, 2015, vol. 80, # 24, p. 11916 - 11925]
[2]Beale, Thomas M.; Moon, Patrick J.; Taylor, Mark S. [Organic Letters, 2014, vol. 16, # 13, p. 3604 - 3607]
[3]Kwon, Ohyun; Danishefsky, Samuel J. [Journal of the American Chemical Society, 1998, vol. 120, # 7, p. 1588 - 1599]
[4]Ahadi, Somayeh; Awan, Shahid I.; Werz, Daniel B. [Chemistry - A European Journal, 2020]

21
[ 13154-24-0 ]
[ 21193-75-9 ]
[ 201053-37-4 ]

Yield	Reaction Conditions	Operation in experiment
93%	With 1H-imidazole In N,N-dimethyl-formamide at 60℃; for 48h;
92%	With 1H-imidazole In N,N-dimethyl-formamide for 12h; Ambient temperature;
84%	With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 18h; Inert atmosphere;

Reference： [1]Leśniak, Stanisław; Malinowska, Martyna; Tracz, Aleksandra; Zawisza, Anna [Molecules, 2022, vol. 27, # 6]
[2]Bettelli, Enzo; Cherubini, Paola; D'Andrea, Piero; Passacantilli, Pietro; Piancatelli, Giovanni [Tetrahedron, 1998, vol. 54, # 22, p. 6011 - 6018]
[3]Takeda, Daiki; Yoritate, Makoto; Yasutomi, Hiroki; Chiba, Suzuka; Moriyama, Takahiro; Yokoo, Atsushi; Usui, Kazuteru; Hirai, Go [Organic Letters, 2021, vol. 23, # 5, p. 1940 - 1944]

22
[ 21193-75-9 ]
1,5-anhydro-2-deoxy-D-threo-hex-1-en-3-ulose [ No CAS ]
[ 3971-47-9 ]

Yield	Reaction Conditions	Operation in experiment
1: 96% 2: 3%	With ethene In acetonitrile at 50℃; for 7h;
1: 36% 2: 49%	With palladium In N,N-dimethyl-formamide at 25℃; for 5h;
	With vinyl acetate In acetonitrile at 50℃;

Reference： [1]Hayashi, Masahiko; Yamada, Kanako; Nakayama, Shuzo [Synthesis, 1999, # 11, p. 1869 - 1871]
[2]Hayashi; Yamada; Arikita [Tetrahedron Letters, 1999, vol. 40, # 6, p. 1171 - 1174]
[3]Hayashi, Masahiko; Yamada, Kanako; Arikita, Osamu [Tetrahedron, 1999, vol. 55, # 28, p. 8331 - 8340]

23
[ 21193-75-9 ]
[ 14086-08-9 ]

Yield	Reaction Conditions	Operation in experiment
82%	With perchloric acid In acetonitrile at 80℃; for 2.5h;
82%	With indium(III) chloride In acetonitrile at 20℃; for 2.5h;
60%	With water In acetonitrile at 80℃; for 0.833333h;

47%

With bismuth(lll) trifluoromethanesulfonate In acetonitrile for 0.0833333h;

Reference： [1]Agarwal, Aditi; Rani, Shikha; Vankar, Yashwant D. [Journal of Organic Chemistry, 2004, vol. 69, # 18, p. 6137 - 6140]
[2]Sobhana Babu; Balasubramanian [Journal of Organic Chemistry, 2000, vol. 65, # 13, p. 4198 - 4199]
[3]Hayashi, Masahiko; Kawabata, Hirotoshi; Yamada, Kanako [Chemical Communications, 1999, # 11, p. 965 - 966]
[4]Lokesh Babu; Khare, Anakshi; Vankar, Yashwant D. [Molecules, 2005, vol. 10, # 8, p. 884 - 892]

24
[ 138459-91-3 ]
[ 21193-75-9 ]
[ 185803-62-7 ]

Yield	Reaction Conditions	Operation in experiment
75%	With sodium hydride In tetrahydrofuran at 0℃;

Reference： [1]Lemee, Lenaick; Jegou, Anne; Veyrieres, Alain [Tetrahedron Letters, 1999, vol. 40, # 14, p. 2761 - 2764]

25
[ 21193-75-9 ]
3-pivaloylthiazolidine-2-thione [ No CAS ]
[ 185803-62-7 ]

Yield	Reaction Conditions	Operation in experiment
75%	With sodium hydride In tetrahydrofuran at 0℃; for 1h;

Reference： [1]Jaouen, Veronique; Jegou, Anne; Lemee, Lenaick; Veyrieres, Alain [Tetrahedron, 1999, vol. 55, # 30, p. 9245 - 9260]

26
[ 141-78-6 ]
[ 21193-75-9 ]
[ 2595-98-4 ]
[ 59-23-4 ]

Reference： [1]Levene; Tipson [Journal of Biological Chemistry, 1931, vol. 93, p. 631,634, 635]

27
[ 160855-18-5 ]
[ 21193-75-9 ]
Acetic acid (7aR,9R,10S,11S,11aR)-10-acetoxy-9-acetoxymethyl-9,10,11,11a-tetrahydro-7aH-7,8-dioxa-12-thia-benzo[a]anthracen-11-yl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	Stage #1: 2-((2-hydroxynaphthalen-1-yl)thio)isoindoline-1,3-dione; D-galactal With pyridine In dimethyl sulfoxide at 60℃; for 4h; Stage #2: Ac-X

Reference： [1]Capozzi, Giuseppe; Falciani, Chiara; Menichetti, Stefano; Nativi, Cristina; Raffaelli, Barbara [Chemistry - A European Journal, 1999, vol. 5, # 6, p. 1748 - 1754]

28
[ 69739-34-0 ]
[ 21193-75-9 ]
[ 124751-19-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	With pyridine at 0℃;

Reference： [1]Bartolozzi, Alessandra; Capozzi, Giuseppe; Menichetti, Stefano; Nativi, Cristina [Organic Letters, 2000, vol. 2, # 3, p. 251 - 253]

29
[ 63-39-8 ]
[ 21193-75-9 ]
uridine 5'-diphospho-2-deoxy-2-fluoro-α-D-galactose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: D-galactal With 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(trifluoromethanesulfonate) In water for 3h; Stage #2: With benzenesulfonamide; ATP at 25℃; for 96h; Enzymatic reaction; Stage #3: UTP With pyrophosphatase at 20℃; for 72h;

Reference： [1]Burkart, Michael D.; Vincent, Stephane P.; Dueffels, Arno; Murray, Brion W.; Ley, Steven V.; Wong, Chi-Huey [Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 8, p. 1937 - 1946]

30
[ 2232-08-8 ]
[ 21193-75-9 ]
3,6-Anhydro-4-O-(p-toluenesulfonyl)-D-galactal [ No CAS ]

Reference： [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2000,vol. 55,p. 317 - 320

31
[ 21193-75-9 ]
[ 209005-34-5 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: D-galactal With 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(trifluoromethanesulfonate) In water at 25℃; for 3h; Stage #2: With phosphonoacetic acid; ATP; bovine albumin at 25℃; for 96h; Enzymatic reaction;

Reference： [1]Burkart, Michael D.; Vincent, Stephane P.; Dueffels, Arno; Murray, Brion W.; Ley, Steven V.; Wong, Chi-Huey [Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 8, p. 1937 - 1946]

32
[ 13154-24-0 ]
[ 21193-75-9 ]
[ 356060-86-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: triisopropylsilyl chloride; D-galactal With 1H-imidazole In N,N-dimethyl-formamide at 20℃; Stage #2: benzoyl haloide

Reference： [1]Graziani, Andrea; Passacantilli, Pietro; Piancatelli, Giovanni; Tani, Simona [Tetrahedron Letters, 2001, vol. 42, # 23, p. 3857 - 3860]

33
[ 85272-31-7 ]
[ 21193-75-9 ]
[ 293294-45-8 ]

Yield	Reaction Conditions	Operation in experiment
87%	Stage #1: di-tert-butylsilyl bis(trifluoromethanesulfonate); D-galactal In N,N-dimethyl-formamide at -45℃; for 1.41667h; Inert atmosphere; Stage #2: With pyridine In N,N-dimethyl-formamide at -45 - 0℃; Inert atmosphere;
83%	With pyridine In N,N-dimethyl-formamide at -40℃; for 0.5h;
80%	With pyridine In dichloromethane at 0℃; for 6h;

72%	Stage #1: di-tert-butylsilyl bis(trifluoromethanesulfonate); D-galactal In N,N-dimethyl-formamide at -40℃; for 1.75h; Stage #2: With pyridine In N,N-dimethyl-formamide for 0.0833333h; Cooling;
68%	With pyridine In N,N-dimethyl-formamide at -40 - 20℃; for 1h; Inert atmosphere;	Compound S1 (4g, 28.2mmol) was dissolved in 40mL DMF, cooled to -40°C, tert-Bu2Si(OTf)2 (10mL, 31.0mmol, 1.1eq) was added and stirred for 1h under N2 protection, and pyridine (4.5mL, 56.4mmol, 2eq) was raised to room temperature. The reaction system was diluted with ethyl acetate, washed with saturated NaCl, dried with anhydrous Na2SO4, filtered with suction, spin-dried the solvent, and passed through the column with (PE:EA=40:1-20:1) to obtain a white solid 2-1 (5.528g) , 68%). 1
56%	Stage #1: di-tert-butylsilyl bis(trifluoromethanesulfonate); D-galactal In N,N-dimethyl-formamide at -40℃; for 0.5h; Stage #2: With pyridine In N,N-dimethyl-formamide for 0.0833333h;
	Stage #1: di-tert-butylsilyl bis(trifluoromethanesulfonate); D-galactal In dichloromethane; N,N-dimethyl-formamide at -45℃; for 1.66667h; Inert atmosphere; Stage #2: With pyridine In dichloromethane; N,N-dimethyl-formamide at -45 - 0℃; Inert atmosphere; regioselective reaction;
	Stage #1: di-tert-butylsilyl bis(trifluoromethanesulfonate); D-galactal In N,N-dimethyl-formamide at -45 - -40℃; Stage #2: With pyridine In N,N-dimethyl-formamide at -40 - 20℃;

Reference： [1]Balmond, Edward I.; Coe, Diane M.; Galan, M. Carmen; McGarrigle, Eoghan M. [Angewandte Chemie - International Edition, 2012, vol. 51, # 36, p. 9152 - 9155]
[2]Abdel-Rahman, Adel A.-H.; Winterfeld, Gottfried A.; Takhi, Mohamed; Schmidt, Richard R. [European Journal of Organic Chemistry, 2002, # 4, p. 713 - 717] Abdel-Rahman, Adel A. -H.; Takhi, Mohamed; El Ashry, El Sayed H.; Schmidt, Richard R. [Journal of Carbohydrate Chemistry, 2002, vol. 21, # 1-2, p. 113 - 122]
[3]Ganesh, Venkataraman; Kundu, Taraknath; Chandrasekaran, Srinivasan [Tetrahedron, 2014, vol. 70, # 40, p. 7268 - 7282]
[4]Location in patent: experimental part Gabrielli, Gabriele; Melani, Fabrizio; Bernasconi, Sara; Lunghi, Carlotta; Richichi, Barbara; Rollin, Patrick; Venturi, Chiara; Nativi, Cristina [Journal of Carbohydrate Chemistry, 2009, vol. 28, # 3, p. 124 - 141]
[5]Current Patent Assignee: JIANGXI NORMAL UNIVERSITY - CN113200951, 2021, A Location in patent: Paragraph 0072-0073
[6]Kobayashi, Yusuke; Masakado, Sota; Takemoto, Yoshiji [Angewandte Chemie - International Edition, 2018, vol. 57, # 3, p. 693 - 697][Angew. Chem., 2017, vol. 130, p. 701 - 705,5]
[7]Chen, Chi-Li; Namba, Kosuke; Kishi, Yoshito [Organic Letters, 2009, vol. 11, # 2, p. 409 - 412]
[8]Jimenez-Barbero, Jesus; Dragoni, Elisa; Venturis, Chiara; Nannucci, Federico; Arda, Ana; Fontanella, Marco; Andre, Sabine; Canada, Francisco Javier; Gabius, Hans-Joachim; Nativi, Cristina [Chemistry - A European Journal, 2009, vol. 15, # 40, p. 10423 - 10431]

34
[ 100-39-0 ]
[ 21193-75-9 ]
[ 81928-98-5 ]
[ 80040-79-5 ]
[ 173008-15-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 36% 2: 26% 3: 20%	With sodium hydride In N,N-dimethyl-formamide at 0℃;

Reference： [1]Bosse, Folkert; Marcaurelle, Lisa A.; Seeberger, Peter H. [Journal of Organic Chemistry, 2002, vol. 67, # 19, p. 6659 - 6670]

35
[ 21193-75-9 ]
[ 161254-77-9 ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: D-galactal With 3 Angstroem MS; bis(tri-n-butyltin)oxide In acetonitrile for 3h; Heating; Stage #2: With iodine In dichloromethane at 0℃; for 0.25h; Further stages.;

Reference： [1]Hawley, Joanne; Bampos, Nick; Aboitiz, Nuria; Jimenez-Barbero, Jesus; Lopez De La Paz, Manuela; Sanders, Jeremy K. M.; Carmona, Pedro; Vicent, Cristina [European Journal of Organic Chemistry, 2002, # 12, p. 1925 - 1936]

36
[ 13154-24-0 ]
[ 21193-75-9 ]
(2R,3S,4R)-4-Triisopropylsilanyloxy-2-triisopropylsilanyloxymethyl-3,4-dihydro-2H-pyran-3-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With 1H-imidazole In N,N-dimethyl-formamide at 60℃; for 18h;

Reference： [1]Dubbaka, Srinivas Reddy; Steunenberg, Peter; Vogel, Pierre [Synlett, 2004, # 7, p. 1235 - 1238]

37
[ 824-94-2 ]
[ 21193-75-9 ]
[ 845884-17-5 ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: D-galactal With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1.5h; Inert atmosphere; Stage #2: p-methoxybenzyl chloride With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide; mineral oil at 20℃; for 14h; Inert atmosphere;
	With sodium hydride In N,N-dimethyl-formamide
8.08 g	Stage #1: D-galactal With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere; Stage #2: p-methoxybenzyl chloride In N,N-dimethyl-formamide at 20℃; for 24.25h; Inert atmosphere;

762 mg	Stage #1: D-galactal With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.333333h; Stage #2: p-methoxybenzyl chloride With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 0℃; for 12h;
	Stage #1: D-galactal With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.333333h; Stage #2: p-methoxybenzyl chloride In N,N-dimethyl-formamide for 12h;

Reference： [1]Location in patent: experimental part Mathew, Thresen; Billaud, Celia; Billich, Andreas; Cavallari, Marco; Nussbaumer, Peter; De Libero, Gennaro; Vasella, Andrea [Chemistry and biodiversity, 2009, vol. 6, # 5, p. 725 - 738]
[2]Postema, Maarten H. D.; Piper, Jared L.; Betts, Russell L.; Valeriote, Frederick A.; Pietraszkewicz, Halina [Journal of Organic Chemistry, 2005, vol. 70, # 3, p. 829 - 836]
[3]Chabre, Yoann M.; Giguere, Denis; Blanchard, Bertrand; Rodrigue, Jacques; Rocheleau, Sylvain; Neault, Mathieu; Rauthu, Subhash; Papadopoulos, Alex; Arnold, Alexandre A.; Imberty, Anne; Roy, Rene [Chemistry - A European Journal, 2011, vol. 17, # 23, p. 6545 - 6562]
[4]Wang, Bang; Xiong, De-Cai; Ye, Xin-Shan [Organic Letters, 2015, vol. 17, # 22, p. 5698 - 5701]
[5]Yu, Changyue; Liu, Yichu; Xie, Xiong; Hu, Shulei; Zhang, Shurui; Zeng, Mingjie; Zhang, Dan; Wang, Jiang; Liu, Hong [Advanced Synthesis and Catalysis, 2021, vol. 363, # 21, p. 4926 - 4931]

38
[ 5460-29-7 ]
[ 21193-75-9 ]
3-O-(3-phthalimidopropyl)-D-galactal [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	Stage #1: D-galactal With bis-dibutyltin oxide In methanol for 2h; Heating; Stage #2: 2-(3-bromopropyl)isoindole-1,3-dione With tetra-(n-butyl)ammonium iodide In toluene at 85℃; for 72h;

Reference： [1]Heidecke, Christoph D.; Lindhorst, Thisbe K. [Synthesis, 2006, # 1, p. 161 - 165]

39
[ 69304-37-6 ]
[ 21193-75-9 ]
[ 660821-35-2 ]

Yield	Reaction Conditions	Operation in experiment
79%	With pyridine at 0℃; for 3h;

Reference： [1]Gonzalez, Concepcion C.; Kennedy, Alan R.; Leon, Elisa I.; Riesco-Fagundo, Concepcion; Suarez, Ernesto [Chemistry - A European Journal, 2003, vol. 9, # 23, p. 5800 - 5809]

40
[ 6959-47-3 ]
[ 21193-75-9 ]
[ 873868-49-6 ]

Yield	Reaction Conditions	Operation in experiment
60%	Stage #1: D-galactal With sodium hydride In N,N-dimethyl-formamide Stage #2: 2-chloromethylpyridine hydrochloride With sodium hydride In N,N-dimethyl-formamide at 20℃; for 17h;

Reference： [1]Bellot, Francois; Hardre, Renaud; Pelosi, Giorgio; Therisod, Michel; Policar, Clotilde [Chemical Communications, 2005, # 43, p. 5414 - 5416]

41
[ 21193-75-9 ]
[ 165816-37-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 36 percent / sodium hydride / dimethylformamide / 0 °C 2: NaH; TBAI / dimethylformamide / 16 h / 0 - 20 °C
	Multi-step reaction with 2 steps 1: 1.) Bu₂SnO, 2.) TBABr / 1.) benzene, reflux, 2 h, 2.) benzene, reflux, 4 h 2: 96 percent / NaH / dimethylformamide / 1.5 h / 0 - 20 °C
	Multi-step reaction with 2 steps 1: 70 percent / n-Bu₂SnO, TBABr / benzene 2: 1.) NaH / 1.) DMF, 2.) DMF

Reference： [1]Bosse, Folkert; Marcaurelle, Lisa A.; Seeberger, Peter H. [Journal of Organic Chemistry, 2002, vol. 67, # 19, p. 6659 - 6670]
[2]Park, Tae Kyo; Kim, In Jong; Hu, Shuanghua; Bilodeau, Mark T.; Randolph, John T.; Kwon, Ohyun; Danishefsky, Samuel J. [Journal of the American Chemical Society, 1996, vol. 118, # 46, p. 11488 - 11500]
[3]Bilodeau, Mark T.; Park, Tae Kyo; Hu, Shuanghua; Randolph, John T.; Danishefsky, Samuel J.; Livingston, Philip O.; Zhang, Shengli [Journal of the American Chemical Society, 1995, vol. 117, # 29, p. 7840 - 7841]

42
[ 21193-75-9 ]
[ 201053-38-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 92 percent / imidazole / dimethylformamide / 12 h / Ambient temperature 2: 100 percent / pyridine / Ambient temperature
	Multi-step reaction with 3 steps 1: Im / dimethylformamide 2: 62 percent / imidazole / dimethylformamide 3: 89 percent / pyridine, DMAP

Reference： [1]Bettelli, Enzo; Cherubini, Paola; D'Andrea, Piero; Passacantilli, Pietro; Piancatelli, Giovanni [Tetrahedron, 1998, vol. 54, # 22, p. 6011 - 6018]
[2]Kwon, Ohyun; Danishefsky, Samuel J. [Journal of the American Chemical Society, 1998, vol. 120, # 7, p. 1588 - 1599]

43
[ 21193-75-9 ]
[ 149625-80-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Im / dimethylformamide 2: 97 percent / 4-dimethylaminopyridine / CH₂Cl₂
	Multi-step reaction with 2 steps 1: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 0 - 20 °C / Inert atmosphere 2: 1H-imidazole / tetrahydrofuran / 10 h / 20 °C / Inert atmosphere

Reference： [1]Kwon, Ohyun; Danishefsky, Samuel J. [Journal of the American Chemical Society, 1998, vol. 120, # 7, p. 1588 - 1599]
[2]Dai, Yuanwei; Zheng, Jianfeng; Zhang, Qiang [Organic Letters, 2018, vol. 20, # 13, p. 3923 - 3927]

44
[ 21193-75-9 ]
(3aS,4R,6R,7R,7aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-((2R,3R,4R)-3-hydroxy-2-triisopropylsilanyloxymethyl-3,4-dihydro-2H-pyran-4-yloxy)-4-triisopropylsilanyloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: Im / dimethylformamide 2: ZnCl₂ / tetrahydrofuran / 12 h / Ambient temperature 3: 100 percent / imidazole / dimethylformamide / Ambient temperature
	Multi-step reaction with 5 steps 1: Im / dimethylformamide 2: 97 percent / 4-dimethylaminopyridine / CH₂Cl₂ 3: dimethyldioxirane / CH₂Cl₂ / 0.67 h / 0 °C 4: ZnCl₂ / tetrahydrofuran / 12 h / Ambient temperature 5: 100 percent / imidazole / dimethylformamide / Ambient temperature