[ CAS No. 42772-85-0 ]

Name: 42772-85-0|2-Hydroxyethyl 4-methylbenzenesulfonate|95%
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Quality Control of [ 42772-85-0 ]

COA NMR CNMR HPLC LC-MS

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Alternatived Products of [ 42772-85-0 ]

Product Details of [ 42772-85-0 ]

CAS No. :	42772-85-0	MDL No. :	MFCD27950701
Formula :	C₉H₁₂O₄S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DZVSAHOHDQUFMZ-UHFFFAOYSA-N
M.W :	216.25	Pubchem ID :	249155
Synonyms :

Calculated chemistry of [ 42772-85-0 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	4
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	51.56
TPSA :	71.98 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.08 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.92
Log Po/w (XLOGP3) :	0.76
Log Po/w (WLOGP) :	1.77
Log Po/w (MLOGP) :	1.25
Log Po/w (SILICOS-IT) :	0.87
Consensus Log Po/w :	1.31

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.71
Solubility :	4.19 mg/ml ; 0.0194 mol/l
Class :	Very soluble
Log S (Ali) :	-1.85
Solubility :	3.04 mg/ml ; 0.0141 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.69
Solubility :	0.44 mg/ml ; 0.00203 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.52

Safety of [ 42772-85-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 42772-85-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 42772-85-0 ]
Downstream synthetic route of [ 42772-85-0 ]

[ 42772-85-0 ] Synthesis Path-Upstream 1~2

1
[ 107-21-1 ]
[ 98-59-9 ]
[ 42772-85-0 ]
[ 6315-52-2 ]

Reference： [1] Tetrahedron, 1987, vol. 43, # 19, p. 4271 - 4276
[2] Liebigs Annalen der Chemie, 1981, # 10, p. 1774 - 1784
[3] Organic Letters, 2002, vol. 4, # 14, p. 2329 - 2332
[4] Polymer, 2011, vol. 52, # 18, p. 3879 - 3886

2
[ 42772-85-0 ]
[ 383-50-6 ]

Reference： [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 25, p. 6473 - 6476[2] Angew. Chem., 2014, vol. 126, # 25, p. 6591 - 6594,4
[3] European Journal of Medicinal Chemistry, 2014, vol. 90, p. 742 - 750
[4] European Journal of Medicinal Chemistry, 2014, vol. 90, p. 742 - 750

[ 42772-85-0 ] Synthesis Path-Downstream 1~68

1
[ 42772-85-0 ]
[ 5962-19-6 ]
(8<i>S</i>,9<i>R</i>)-6'-(2-hydroxy-ethoxy)-10,11-dihydro-cinchonan-9-ol [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1935,vol. 57,p. 575,577

2
[ 42772-85-0 ]
[ 52096-02-3 ]
[ 52096-11-4 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1973,p. 2503 - 2506

3
[ 42772-85-0 ]
[ 4980-90-9 ]
[ 4863-04-1 ]

Reference： [1]Journal of medicinal chemistry,1966,vol. 9,p. 165 - 168

4
[ 75-21-8 ]
[ 7182-86-7 ]
[ 42772-85-0 ]
[ 667-32-3 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1987,vol. 23,p. 1264 - 1279
Zhurnal Organicheskoi Khimii,1987,vol. 23,p. 1402 - 1419

5
[ 110-86-1 ]
[ 42772-85-0 ]
2-hydroxyethylpyridinium p-toluenesulfonate [ No CAS ]

Reference： [1]Il Farmaco,1993,vol. 48,p. 573 - 613

6
[ 110-87-2 ]
[ 42772-85-0 ]
<2-(Tetrahydro-2-pyranyloxy)ethyl>-p-toluolsulfonat [ No CAS ]

Reference： [1]Liebigs Annalen der Chemie,1981,p. 1774 - 1784

7
[ 288-47-1 ]
[ 42772-85-0 ]
2-hydroxyethylthiazolium p-toluenesulfonate [ No CAS ]

Reference： [1]Il Farmaco,1993,vol. 48,p. 573 - 613

8
[ 96-49-1 ]
[ 6192-52-5 ]
[ 42772-85-0 ]

Reference： [1]Chemical and pharmaceutical bulletin,1985,vol. 33,p. 1380 - 1386

9
[ 112-31-2 ]
[ 42772-85-0 ]
[ 115147-99-4 ]

Reference： [1]Tetrahedron,1987,vol. 43,p. 4271 - 4276

10
[ 42772-85-0 ]
[ 124-13-0 ]
[ 115147-98-3 ]

Reference： [1]Tetrahedron,1987,vol. 43,p. 4271 - 4276

11
[ 6123-63-3 ]
[ 107-21-1 ]
[ 6831-91-0 ]
[ 42772-85-0 ]
[ 19859-09-7 ]
[ 90433-97-9 ]

Reference： [1]Journal of Organic Chemistry,1984,vol. 49,p. 2663 - 2669

12
[ 6123-63-3 ]
[ 6831-91-0 ]
[ 42772-85-0 ]
[ 19859-09-7 ]
[ 90433-97-9 ]

Reference： [1]Journal of Organic Chemistry,1984,vol. 49,p. 2663 - 2669

13
[ 542-59-6 ]
[ 6192-52-5 ]
[ 107-21-1 ]
[ 42772-85-0 ]
[ 19859-09-7 ]

Reference： [1]Journal of Organic Chemistry,1984,vol. 49,p. 2663 - 2669

14
[ 107-21-1 ]
[ 98-59-9 ]
[ 42772-85-0 ]
[ 6315-52-2 ]

Yield	Reaction Conditions	Operation in experiment
57%; 17%		Ethylene glycol monotosylate and ethylene glycol ditosylatewere prepared using a procedure similar to one described previously[53]. Briefly, ethylene glycol (3.5 mL, 62.9 mmol, 8.0 eq.),triethylamine (3.3 mL, 23.6 mmol, 3.0 eq.), and dicholoromethathane(CH2Cl2, 12 mL) were added to a flask and stirred at0 C for 20 min. A solution of TsCl (1.5 g, 7.9 mmol, 1.0 eq.) in CH2Cl2(13 mL) was added slowly using a syringe over 1 h. The resultingmixturewas warmed to room temperature and stirred for 24 h. TLCindicated complete consumption of TsCl. The reaction mixture waswashed with water (2 10 mL), and the aqueous layer wasextracted with CH2Cl2. Organic layers were combined and evaporated.The products were purified by flash column chromatographyon silica gel using 30% ethyl acetate (EtOAc)/hexanes (Hex) to yieldethylene glycol monotosylate as a colorless oil (970 mg, 57% yield)with >95% purity and ethylene glycol ditosylate as a white crystallinesolid (490 mg, 17% yield) with >96% purity. Ethylene glycolmonotosylate: Rf 0.3 in 30% EtOAc/Hex; 1H NMR (CDCl3,500 MHz) d: 7.81 (d, J 7.1, 2H), 7.36 (d, J 7.1 Hz, 2H), 4.14 (q,J 2.3 Hz, 2H), 3.82 (t, J 1.9 Hz, 2H), 2.45 (s, 3H). Ethylene glycolditosylate: Rf 0.5 in 30% EtOAc/Hex; 1H NMR (CDCl3, 500 MHz) d:7.73 (d, J 8.1 Hz, 2H), 7.34 (d, J 7.7 Hz, 2H), 4.18 (s, 2H), 2.46 (s,3H).

Reference： [1]Tetrahedron,1987,vol. 43,p. 4271 - 4276
[2]Liebigs Annalen der Chemie,1981,p. 1774 - 1784
[3]Organic Letters,2002,vol. 4,p. 2329 - 2332
[4]European Journal of Medicinal Chemistry,2019,vol. 182
[5]Polymer,2011,vol. 52,p. 3879 - 3886

15
[ 42772-85-0 ]
[ 123-72-8 ]
[ 115147-97-2 ]

Reference： [1]Tetrahedron,1987,vol. 43,p. 4271 - 4276

16
[ 42772-85-0 ]
[ 49780-25-8 ]
[ 104575-26-0 ]

Reference： [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 150 - 156

17
[ 42772-85-0 ]
[ 139-02-6 ]
[ 74-88-4 ]
[ 41532-81-4 ]

Reference： [1]Tetrahedron,1976,vol. 32,p. 1741 - 1743

18
[ 42772-85-0 ]
[ 3095-94-1 ]
C₁₇H₂₈ClO₅PS [ No CAS ]

Reference： [1]Chemical Research in Toxicology,1995,vol. 8,p. 1070 - 1076

21
[ 104-15-4 ]
[ 107-21-1 ]
[ 42772-85-0 ]

Yield	Reaction Conditions	Operation in experiment
34%	With pyridine; at 20℃; for 6h;	General procedure: 39a-d (78.68 mmol) and p-toluenesulfonic acid (39.34 mmol) weredissolved in pyridine (10 mL). The mixture was stirred at room temperaturefor 6 h, then 1 M HCl (20 mL) was added dropwise, and a largeamount of solid salt was precipitated. After filtration, the filtrate wasextracted with ethyl acetate. The organic layer was dried over anhydroussodium sulfate and concentrated under reduced pressure to give40a-d.

Reference： [1]Tetrahedron,2000,vol. 56,p. 7291 - 7298
[2]Bioorganic and Medicinal Chemistry,2020,vol. 28

22
[ 107-21-1 ]
[ 98-59-9 ]
[ 42772-85-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	With triethylamine; at 25 - 40℃; for 1h;	p-Toluenesulfonyl chloride (10.0 g, 0.052 mmol) was added to ethylene glycol (180 mL, 3.23 mmol) with stirring. The mixture was stirred for 30 min at rt. Triethylamine (7.24 mL, 0.052 mmol) was then added dropwise in the course of 5 min and the reaction mixture?s temperature has raised spontaneously to approximately 40 C. Course of the reaction was monitored by TLC (hexane/EtOAc 1:1) and detected with (UV light 254 nm and subsequent dipping in solution of 0.5% KMnO4 and 4% NaOH in H2O). After 1 h the reaction was complete. The mixture was transferred to a separatory funnel with H2O (400 mL) and CHCl3 (400 mL). After shaking, the organic phase was separated and the H2O phase was extracted with another 200 mL of CHCL3. Organic extracts were merged, dried with anhydrous MgSO4 and evaporated in vacuo. The reaction afforded product 21 (10.04 g) as clear colorless viscous liquid in 92% yield.
81%	With pyridine; dmap; at 25℃; for 2h;Inert atmosphere;	Ethylene glycol (6.71 mL, 120 mmol)Was dissolved in pyridine (2.90 mL, 36.0 mmol)4-Dimethylaminopyridine (36.7 mg, 0.300 mmol) was added.below freezing,4-methylbenzene-1-sulfonyl chloride (5.72 g, 30.0 mmol) was added,Under an argon atmosphere,And the mixture was stirred at room temperature (25 C.) for 2 hours.After completion of the reaction,After dilution with dichloromethane, 0.5 mol / L hydrochloric acid was added.Extraction was carried out three times with dichloromethane,The combined dichloromethane layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure,The obtained crude product was purified by silica gel chromatography (eluent (volume ratio): hexane / ethyl acetate = 2/1)2 - [(4-methylbenzenesulfonyl) oxy] ethan-1-ol (5.27 g, 24.4 mmol, yield based on 4-methylbenzene-1-sulfonyl chloride: 81%).
75%	With triethylamine; at 20 - 40℃; for 1.58333h;	Protocole 2 p-Toluenesulfonyl chloride (310 mmol ; 6.00 g ) was added to ethylene glycol (940 mmol ; 53 mL). The mixture was stirred for 30 min at room temperature, triethylamine (310 mmol ; 4.4 mL) was then added dropwise in the course of 5 min and the reaction mixture?s temperature has raised spontaneously to approximately 40C. After 1 h the reaction was complete. The mixture was transferred to a separatory funnel with water (200 mL) and CH2Cl2 (200 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (200 mL), dried over MgSO4, filtered and concentrated under reduce pressure. The residue was purified by flash column chromatography on silica gel (99% CH2Cl2/MeOH) to afford the desired product 3a as clear yellow oil in 75% yield (5.02 g).

56%	With pyridine; dmap; at 20℃; for 1.5h;	EXAMPLE 1 Toluene-4-Sulfonic Acid 2-Hydroxy-Ethyl Ester (Reagent 1) A mixture of HO(CH2)2OH, (2.5 g, 40 mmol), TsCl (1.90 g, 10 mmol), pyridine (1.1 g, 12 mmol) and DMAP (12 mg, 0.1 mmol) was stirred at room temperature for 1.5 h. The reaction mixture was partitioned between CH2Cl2 (20 mL) and 0.5 M hydrochloric acid (10 mL*2). The organic layer was dried over Na2 SO4, and concentrated in vacuo. The resultant residue was purified by chromatography on silica gel (eluted with petroleum ether:ethyl acetate=4:1) to give reagent 1 as colorless oil (1.2 g, 56% yield).
46%	With potassium iodide; silver(l) oxide; In dichloromethane; at 20℃; for 1h;	Fresh silver oxide (350 mg, 1.5 mmol), p-toluenesulfonyl chloride (210 mg, 1.1 mmol) and potassium iodide (33 mg, 0.2 mmol) were added to a stirred solution of 1,2- ethanediol (62 mg, 1 mmol) in dichloromethane (10 ml). The reaction mixture was stirred at room temperature for 1 hour, filtered through a small pad of celite and washed with ethyl acetate. The solvent was removed and the crude product was purified by column chromatography (CH2Cl2MeOH, 40:1 v/v as eluent) to yield the monotosylate product 7 as transparent oil in 46% yield. 1H n.m.r. (CDCl3, 300 MHz) delta: 7.81 (d, 2H, J = 8.1), 7.36 (d, 2H, J= 8.1), 4.15(d, 2H, J= 9.0), 3.82 (d, 2H, J= 9.0), 2.46 (s, 3H).
33.58%	With pyridine; at 20℃; for 4h;	Ethylene glycol (4.00 g, 64.05 mmol) was dissolved in 5 mL pyridine and p-toluenesulfonyl chloride was added in portions (6.14g,32.22 mmol), after stirring at room temperature for 4 hours, 6 mol/L hydrochloric acid (40 mL) was added, extracted with ethyl acetate, and washed with saturated brine.The organic layer was collected and dried over anhydrous sodium sulfate. The organic solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography usingThe petroleum ether/ethyl acetate (V/V=20/1-10/1) eluted to give a colorless liquid, weighed 2.34 g, and the yield was 33.58%.
32%		To ethylene glycol (130 mL), 60% sodium hydride (4.83 g, 120.6 mmol) was gradually added in argon atmosphere at room temperature with stirring, and stirred for 40 min, and toluene sulfonyl chloride (20.00 g, 104.9 mmol) was further added and stirred for 6 hours at the same temperature. Dichloromethane (100) was added to this reaction mixture, and stirred for 16 hours at room temperature. The reaction mixture was added cold water, and extracted with ethyl acetate. The extract was washed with water, dried, and evaporated to dryness under reduced pressure, and the residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate = 5/1 to 1/1), to obtain 8 (7.30 g, 32%) of oily colorless substance.
29.39%	With pyridine; at 20℃; for 4h;	Ethylene glycol (3.91 g, 62.95 mmol) was dissolved in 5 mL of pyridine and p-toluenesulfonyl chloride (6 g,31.47 mmol). After stirring at room temperature for 4 hours, 6 mol / L hydrochloric acid (40 mL) was added, extracted with ethyl acetate, washed with saturated brine, The organic layer was collected, dried over anhydrous sodium sulfate, and the organic solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography using Petroleum ether / ethyl acetate (V / V = 20 / 1-10 / 1) to give a colorless liquid weighing 2 g and a yield of 29.39%.
29.39%	With hydrogenchloride; In pyridine; at 20℃; for 4h;	Ethylene glycol (3.91 g, 62.95 mmol) was bathed in 5 mL of pyridine.P-toluenesulfonyl chloride (6 g, 31.47 mmol) was added in portions.After stirring at room temperature for 4 hours,6 mol/L hydrochloric acid (40 mL) was added, and the mixture was extracted with ethyl acetate and washed with saturated brine.The organic layer was collected, dried over anhydrous sodium sulfate, and the organic solvent was evaporated under reduced pressure.The residue was purified by silica gel column chromatography.Elution with petroleum ether/ethyl acetate (V/V=20/1-10/1) gave a colorless liquid.Weighing 2g, the yield is 29.39%.
29.39%	With pyridine; at 20℃; for 4h;	Ethylene glycol (3.91g, 62.95mmol) was dissolved in 5mL of pyridine, was added portionwise p-toluenesulfonyl chloride (6g, 31.47mmol), stirred at room temperature for 4 hours, 6mol / L hydrochloric acid (40 mL), extracted with ethyl acetate extracted, washed with brine, the organic layer was collected, dried over anhydrous sodium sulfate, the organic solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography, using petroleum ether / ethyl acetate (V / V = 20 / 1-10 / 1) to afford a colorless liquid, heavy 2g, a yield of 29.39%.
29%	With pyridine; at 20℃; for 4h;	To a solution of compound 26a (3.91 g, 62.95 mmol) in pyridine (5 mL) was added paratoluensulfonyl chloride (6 g, 31.47 mmol) in portions and then stirred at room temperature for 4 h. The reaction mixture was acidified with 6 N HCl and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo.The residue was purified by column chromatography on silica gel(EtOAc/petroleum ether, 1/10) to afford 27a (2 g, 29%) as a colorless liquid. 1H NMR (300 MHz, CDCl3) delta (ppm): 7.81 (d, J = 8.3 Hz, 2H),7.36 (d, J = 8.0 Hz, 2H), 4.16-4.12 (m, 2H), 3.85-3.78 (m, 2H), 2.45(s, 3H), 2.01 (d, J = 19.0 Hz, 1H).
23%	With triethylamine; In dichloromethane; at 40℃; for 12h;	Ethylene glycol (500 mg, 8.1 mmol) and triethylamine (0.54 mL, 4.0 mmol) were dissolved in 7.5 mL dry CH2Cl2, and then TsCl (384 mg, 2.0 mmol) was added into the mixture. The reaction mixture was stirred 12 h at 40C. The resulting mixture was diluted with CH2Cl2, washed with saturated aqueous NH4Cl , NaHCO3 and NaCl successively, and dried over anhydrous Na2SO4. After concentrated in vacuo, the residue was purified by column chromatography (CH2Cl2/MeOH = 20:1) to give 15a (260mg, 23%) as colorless oil. 1HNMR(CDCl3, 400MHz) delta 2.45 (3H, s, -CH3), 3.81 (2H, t, J = 4.4Hz, -CH2OH), 4.13 (2H, t, J = 4.8Hz, TsOCH2-), 7.36 (2H, d, J = 8.0Hz, H-3, H-5 of Ph), 7.81 (2H, d, J= 8.4 Hz, H-2, H-6 of Ph). 13CNMR(CDCl3, 100MHz) delta 145.20, 132,71, 130.06 (2C), 128.05 (2C), 71.75, 60.75, 21.75. MS (ESI) m/z: 217.1 (M + H)+, 239.0 (M + Na)+. The spectroscopic data of 15a were consistent with the reference. S7
8.5%		A mixture of ethylene glycol 9 (5 ml, 89.72 mmol) andtriethylamine (6.25 ml, 44.86 mmol) in 6 ml DCM wasstirred for 30 min. )en, tosyl chlor1i0de (8.55 g,44.80 mmol) was added dropwise for about 30 min. )ereaction was stirred overnight. )e reaction was diluted with70 ml DCM and washed with 1M HCl (50 ml). )e solventwas removed under reduced pressure and semisolid productwas obtained. )e crude was puri7ed by Bash chromatographyusing Hexane : EtOAc (1 : 1). An oily pale yellowproduct was obtained (Yield 8.5%, 1.65 g, 7.63 mmol). Rf: 0.4(Hexane/EtOAc 1 : 1). 1H NMR (500 MHz, CDCl3): * 7.79(d, 2H, J 8.4 Hz, H2OTs), 7.34 (d, 2H, J 7.9 Hz, H2OTs),4.11 (t, 2H, J 4.3 Hz, CH2O), 3.79 (t, 2H, J 4.6 Hz, CH2O),2.42 (s, 3H, CH3), 2.00 (bs, 1H, OH). 13C NMR (125 MHz,CDCl3): * 145.1, 132.6, 130.0, 128.0, 71.7, 60.7, 21.7.
	With sodium iodide; silver(l) oxide; In dichloromethane; at 0℃; for 2h;	621 mg (corresponding to 10.0 mmol) of ethylene glycol was dissolved in 100 mL of methylene chloride. To this solution under an ice bath, 3.49 g (corresponding to 15.0 mmol) of silver oxide, 350 mg (corresponding to 2.1 mmol) of potassium iodide and 2.10 g (corresponding to 11.0 mmol) of p-toluenesulfonylchloride were added. The resulting mixture was stirred at 0C for 2 hours. Insoluble matters were filtered out of the reaction mixture, and were washed with ethyl acetate. The washings were combined with the filtrate, and the mixture was concentrated. The resulting crude product was purified by flash silica gel column chromatography (elution solvent: hexane/ethyl acetate = 1/1) to obtain 643 mg (corresponding to 2.97 mmol) of 2-hydroxyethyl-p-toluenesulfonate (Fig. 1-3, Step3).;
7.74 g	With pyridine; In dichloromethane; at 0 - 20℃;	[0255] A solution of p-toluenesulfonyl chloride (7 g) in dichloromethane (anhydrous, 50 ml) was added dropwise at 0 C to a stirred solution of ethylene glycol (anhydrous, 20 ml) in dichloromethane (anhydrous, 100 ml) and pyridine (anhydrous, 7 ml). The resulting mixture was stirred at room temperature overnight and then poured on ice and allowed to reach room temperature. The reaction mixture was extracted with dichloromethane (3 x 100 ml) and the combined organic phase was washed sequentially with water (150 ml), sulfuric acid (2%, 100 ml), water (150 ml), saturated sodium bicarbonate (150 ml) and again with water (150 ml). Removing the solvent under reduced pressure yielded O-tosyl ethylene glycol 7.74g as a colorless oil.

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[3]Patent: JP2015/110563,2015,A .Location in patent: Paragraph 0016; 0082; 0083
[4]Bioorganic Chemistry,2020,vol. 96
[5]Angewandte Chemie - International Edition,2014,vol. 53,p. 14230 - 14234
Angew. Chem.,2014,vol. 126,p. 14454 - 14458,5
[6]Angewandte Chemie - International Edition,2014,vol. 53,p. 3854 - 3858
Angew. Chem.,2014,vol. 126,p. 3934 - 3939,5
[7]Patent: US2008/96903,2008,A1 .Location in patent: Page/Page column 20
[8]Tetrahedron Letters,2010,vol. 51,p. 6093 - 6097
[9]Patent: WO2007/134362,2007,A1 .Location in patent: Page/Page column 23
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[11]Patent: CN107698575,2018,A .Location in patent: Paragraph 0097-0099
[12]Patent: EP2103611,2009,A1 .Location in patent: Page/Page column 50
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[23]Patent: CN110420334,2019,A .Location in patent: Paragraph 0091-0092; 0097

23
[ 868072-17-7 ]
[ 42772-85-0 ]
[ 958233-17-5 ]

Yield	Reaction Conditions	Operation in experiment
85%	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; for 20h;	Diisopropyl azodicarboxylate (DIAD, 0.48 ml, 2.4 mmol) was added to a solution of 6 (400 mg, 1.1 mmol) triphenylphosphine (637 mg, 2.4 mmol) and 2-hydroxyethyl tosylate (525 mg, 2.4 mmol) in dry THF (10 ml). The reaction mixture was stirred for 20 hours at room temperature and evaporated to dryness. The residue was purified by silica gel column chromatography (CHQ3/Me0H, 80:1 v/v as eluent) to yield 8 as light yellow crystals in 85% yield. 1H n.m.r. (CDCl3, 300 MHz) delta: 7.83 (d, 2H, J= 8.1), 7.74 (d, 2H, J= 9.0), 7.35 (d, 2H, J= 8.1), 6.86 (d, 2H, J= 9.0), 6.52 (s, IH), 4.37 (d, 2H, J= 4.8), 4.19 (d, 2H, J= 4.8), 3.92 (s, 2H), 3.39-3.52 (m, 4H), 2.74 (s, 3H)5 2.56 (s, 3H), 2.45 (s, 3H), 1.08-1.23 (m, 6H); (Found, C, 63.37; H, 5.96; N, 9.89. Mass Spectrum: CI5 m/z 551 (M + 1).

Reference： [1]Patent: WO2007/134362,2007,A1 .Location in patent: Page/Page column 20-21; 23

24
[ 42772-85-0 ]
[ 608-33-3 ]
1,3-dibromo-2-(3-hydroxy-1-oxapropyl)benzene [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 1083 - 1085

25
[ 42772-85-0 ]
C₁₇H₂₈FO₅PS [ No CAS ]

Reference： [1]Chemical Research in Toxicology,1995,vol. 8,p. 1070 - 1076

26
[ 42772-85-0 ]
[ 80158-32-3 ]

Reference： [1]Liebigs Annalen der Chemie,1981,p. 1774 - 1784

27
[ 42772-85-0 ]
[ 80158-33-4 ]

Reference： [1]Liebigs Annalen der Chemie,1981,p. 1774 - 1784

28
[ 42772-85-0 ]
[ 41928-70-5 ]
2-[[(4-methylphenyl)sulfonyl]oxy]ethyl (E)-[(phenylmethoxy)imino]acetate [ No CAS ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 1270 - 1284

29
[ 873436-97-6 ]
[ 42772-85-0 ]
[ 1020728-43-1 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl-formamide; at 60℃; for 3h;	2-[6-Amino-2-fluoro-8-(6-iodo-benzo[1,3]dioxol-5-ylmethyl)-purin-9-yl]-ethanol A mixture of 2-Fluoro-8-(6-iodo-benzo[1,3]dioxol-5-ylmethyl)-9H-purin-6-ylamine (compound 5) (40 mg, 0.1 mmol), TsO(CH2)2 OH (compound 7a, 160 mg) and Cs2CO3 (40 mg, 0.12 mmol) in anhydrous DMF (1 mL) was heated at 60 C. for 3 h. TLC showed the reaction was complete. The solvent was removed under reduced pressure, and the residue was purified by chromatography on silica gel (eluted with EtOAc/hexanes/CHCl3/i-PrOH=10:10:10:1) to give crude compound 8.1a (15 mg), which was used in the next step without further purification.

Reference： [1]Patent: US2008/96903,2008,A1 .Location in patent: Page/Page column 21

30
[ 42772-85-0 ]
[ 956499-75-5 ]
[ 958641-66-2 ]

Yield	Reaction Conditions	Operation in experiment
	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; N,N-dimethyl-formamide; at 20℃; for 17h;	To 10 mL of a solution of 639 mg (corresponding to 2.95 mmol) of 2-hydroxyethyl-p-toluenesulfonate in tetrahydrofran, 388 mg (corresponding to 1.34 mmol) of 6-bromo-2-(4'-hydroxyphenyl)imidazo[1,2-a]pyridine and 780 mg (corresponding to 2.97 mmol) of triphenylphosphine were added. Further, 6 mL of N,N-dimethylformamide was added thereto to completely dissolve the contents. To the reaction mixture, 0.58 mL (corresponding to 2.95 mmol) of diisopropylazodicarboxylate was added. After the reaction mixture was stirred at room temperature for 17 hours, the reaction solution was concentrated. The resulting crude product was purified by flash silica gel column chromatography (elution solvent: hexane/ethyl acetate = 65/35). Insoluble matter in chloroform was filtered out of fractions containing a target compound. Further, the resulting crude product was purified by recycle preparative HPLC (HPLC apparatus: LC-908 (under trade name; manufactured by Japan Analytical Industry Co., Ltd.); column: two JAIGEL 2H (under trade name; manufactured by Japan Analytical Industry Co., Ltd.) connected together; mobile phase: chloroform), to obtain 79.7 mg (corresponding to 164 mumol) of 6-bromo-2-[4'-(2"-p-toluenesulfonyloxyethoxy)phenyl]imidazo[1,2-a]pyridine (Fig. 1-3, Step 4). The NMR measurement results of the resulting 6-bromo-2-[4'-(2"-p-toluenesulfonyloxyethoxy)phenyl]imidazo[1,2-a]pyridine are shown below. NMR apparatus employed: JNM-ECP-500 (manufactured by Japan Electron Optics Laboratory Co., Ltd. (JEOL)) 1H-NMR (solvent: dimethylformamide-d7, resonance frequency: 500 MHz): delta 8.73-8.71 (m, 1H), 8.19-8.17 (m, 1H), 7.81-7.77 (m, 2H), 7.73-7.70 (m, 2H), 7.41-7.38 (m, 1H), 7.39-7.36 (m, 2H), 7.20 (dd, J = 9.5, 1.9 Hz), 6.85-6.81 (m, 2H), 4.34-4.31 (m, 2H), 4.19-4.15 (m, 2H). 13C-NMR (solvent: dimethylformamide-d7, resonance frequency: 125 MHz): delta 158.32, 145.91, 145.24, 143.84, 133.15, 130.18, 127.83, 127.54, 127.19, 127.15, 126.90, 117.56, 114.86, 108.73, 105.80, 69.28, 65.88, 20.69.

Reference： [1]Patent: EP2019103,2009,A1 .Location in patent: Page/Page column 13-14

31
[ 42772-85-0 ]
3-(5-(4-methoxybenzyloxy)-4-oxo-4H-pyran-2-yl)acrylic acid [ No CAS ]
C₁₈H₁₈O₇ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 188 - 191

32
[ 42772-85-0 ]
[ 1163144-41-9 ]
[ 1163144-42-0 ]

Yield	Reaction Conditions	Operation in experiment
4%	With di-isopropyl azodicarboxylate; triphenylphosphine; In N,N-dimethyl-formamide; at 20℃; for 20h;Product distribution / selectivity;	Preparation of 2-(4-(3-(2-(diethylamino)-2-oxoethyl)-6,8-dimethylimidazo[1 ,2- b]pyridazin-2-yl)phenoxy)ethyl 4-methylbenzenesulfonate (8); Method A; Diisopropyl azodicarboxylate (DIAD, 0.21 ml_, 1.1 mmol) was added to a solution of 7 (176 mg, 0.5 mmol) triphenylphosphine (285 mg, 1.1 mmol) and toluene-4-sulfonic acid 2-hydroxy-ethyl ester (235 mg, 1.1 mmol) in anhydrous DMF (10 ml_). The reaction mixture was stirred for 20 h at rt and then concentrated in vacuo (95C, 20 mbar). The resulting crude oil was dissolved in CHCI3 (40 ml.) and washed with water (3 * 20 ml.) to remove traces of DMF. The organic layer was isolated and dried over anhydrous Na2SO4. The solvent was removed in vacuo and the residue was purified by column chromatography (CHCI3ZMeOH, 80:1 v/v as eluent) to yield 8 (10 mg, 0.018 mmol) as pale yellow crystals in 4% yield. 1H NMR (CDCI3, 300 MHz) delta: 1.13-1.28 (m, 6H), 2.45 (s, 3H), 2.49 (s, 3H), 2.63 (s, 3H), 3.42-3.58 (m, 4H), 4.10 (s, 2H), 4.16-4.20 (m, 2H), 4.37-4.40 (m, 2H), 6.70 (s, 1 H), 6.85 (d, J = 6.9 Hz, 2H), 7.34 (d, J = 7.8 Hz, 2H), 7.76 (d, J = 6.9 Hz, 2H), 7.84 (d, J = 7.8 Hz, 2H).

Reference： [1]Patent: WO2009/79683,2009,A1 .Location in patent: Page/Page column 41-42

33
[ 42772-85-0 ]
[ 882175-40-8 ]
[ 1143506-04-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 1464 - 1473

34
[ 42772-85-0 ]
[ 1036392-91-2 ]
[ 943527-56-8 ]

Yield	Reaction Conditions	Operation in experiment
48%	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃;Cooling with ice;	To tetrahydrofuran solution (20 ml) of 11 (0.50 g, 1.52 mmol), 8 (0.72 g, 3.34 mmol) and triphenylphosphine (0.88 g, 3.34 mmol) were added, and diisopropyl azodicarboxylate (0.66 ml, 3.34 mmol) was dropped while ice-cooling with shaking, and stirred at room temperature for 16 hours. The reaction mixture was evaporated to dryness under reduced pressure, and the residue was purified by silica gel column chromatography (solvent: toluene/ethyl acetate = 2/1), and recrystallized with ethyl acetate, to obtain 12 (0.38 g, 48%) of orange crystal. mp 168?169C,1H NMR(300MHz,CDCl3)delta 2.44(3H,s),3.55?3.62(4H,m),3.77?3.87(4H,m), 4.11?4.22(2H,m), 4.37?4.43(2H,m),6.38(1H,d,J=15.7Hz),6.78(1H,dd,J=8.7,2.3Hz) ,6.90(1H,d,J=2.3Hz),7.34(2H,dd,J=7.6,0.7Hz),7.37(1H,s),7.49 (1H,d,J=8.7Hz),7.67(1H,d,J=15.7Hz),7.71?7.84(2H,m) IR (Nujol) 1633cm-1,APCI-MS m/z528[M+H]+

Reference： [1]Patent: EP2103611,2009,A1 .Location in patent: Page/Page column 50-51

35
[ 98-59-9 ]
[ 42772-85-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium iodide; In dichloromethane; ethylene glycol;	, Step 2). 621 mg (corresponding to 10.0 mmol) of ethylene glycol was dissolved in 100 mL of methylene chloride. To this solution under an ice bath, 3.49 g (corresponding to 15.0 mmol) of silver oxide, 350 mg (corresponding to 2.1 mmol) of potassium iodide and 2.10 g (corresponding to 11.0 mmol) of p-toluenesulfonylchloride were added. The resulting mixture was stirred at 0C for 2 hours. Insoluble matters were filtered out of the reaction mixture, and were washed with ethyl acetate. The washings were combined with the filtrate, and the mixture was concentrated. The resulting crude product was purified by flash silica gel column chromatography (elution solvent: hexane/ethyl acetate = 1/1) to obtain 643 mg (corresponding to 2.97 mmol) of 2-hydroxyethyl-p-toluenesulfonate (

Reference： [1]Patent: EP2218463,2010,A1

36
[ 42772-85-0 ]
[ 762-21-0 ]
[ 1258047-78-7 ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 6093 - 6097

37
[ 42772-85-0 ]
[ 623-47-2 ]
[ 1258047-89-0 ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 6093 - 6097

38
[ 42772-85-0 ]
[ 626-41-5 ]
[ 1256728-75-2 ]

Reference： [1]Dalton Transactions,2015,vol. 44,p. 8478 - 8487
[2]Journal of the American Chemical Society,2010,vol. 132,p. 15930 - 15932

39
[ 14282-76-9 ]
[ 42772-85-0 ]
[ 159144-69-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 3237 - 3242

40
[ 948313-69-7 ]
[ 42772-85-0 ]
R(-)-2-tosyloxyethoxy-10,11-hydroxy-N-propylnoraporphine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8%		Example 22. Synthesis of R(-)-2-(2-p- Toluenesulfonyloxy)ethoxy-NPA(15b).; A mixture of N-n-propylnororipavine (460 mg, 1.4 mmol), MeSO3H (5.0 mL) and 2-p-tosyloxyethanol (1.0 g) was stirred for 30 min at 0 C. The mixture was warmed to rt slowly and then warmed up to 95 C stirring for 30 min at this temperature. After cooling to room temperature, the mixture was poured into ice water and basified to pH = 9-10 with ammonium hydroxide. The mixture was extracted with CH2C12 (50 mLx3). The combined organic layer was washed with brine, dried with Na2SO4, and evaporated in vacuo. The residue was purified on silica gel column eluting with CH3OH: CH2C12 = 1: 10 (Rf = 0.5) obtaining 12b (42 mg) in 8% yield pale white foam. The free base was converted to HC1 salt with IN HC1 in ether. 1H NMR (300 MHz, CDC13) delta 7.78 (d, J = 8.2 Hz, 2H), 7.69 (d, J = 2.0 Hz, 1H), 7.28 (d, J = 8.2 Hz, 2H), 6.52 (s, 2H), 6.38 (d, J = 2.0 Hz, 1H), 5.33 (br, s, 2H), 4.30 (t, J = 4.5 Hz, 2H), 4.08 (m, 2H), 3.35 (m, 1H), 3.19-3.07 (m, 2H), 2.96-2.83 (m, 2H), 2.66-2.46 (m, 4H), 2.37 (s, 3H), 1.63-1.60 (m, 2H), 0.93 (t, J = 7.2 Hz, 3H); 13C NMR (base, 75 MHz, CDC13) delta 156.3, 144.9, 143.7, 143.0, 133.6, 133.4, 132.6, 129.8, 128.1, 127.9, 126.9, 120.2, 118.8, 113.9, 112.6, 68.3, 65.3, 59.3, 55.5, 50.6, 48.6, 33.9, 21.5, 18.4, 11.9.

Reference： [1]Patent: WO2011/130530,2011,A1 .Location in patent: Page/Page column 46

41
[ 42772-85-0 ]
[ 108895-98-3 ]
[ 153826-05-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 6389 - 6392

42
[ 42772-85-0 ]
(2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-3-yl)carbamic acid benzyl ester [ No CAS ]
[ 1355613-71-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 6389 - 6392

43
[ 42772-85-0 ]
[ 7385-67-3 ]
[ 1315483-37-4 ]

Reference： [1]Bulletin of the Korean Chemical Society,2011,vol. 32,p. 741 - 744

44
[ 42772-85-0 ]
[ 5787-50-8 ]
[ 713-46-2 ]
[ 113487-25-5 ]

Reference： [1]Polymer,2011,vol. 52,p. 3879 - 3886

45
[ 42772-85-0 ]
[ 1832-64-0 ]
[ 1428268-08-9 ]

Yield	Reaction Conditions	Operation in experiment
	With dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 24h;	General procedure: To 4-nitrophenyl hydrogen alkylphosphonate (0.5 mmol) in dry CH2Cl2 (5 mL) was added the 2/3-haloalcohol or <strong>[42772-85-0]2-hydroxyethyl 4-methylbenzenesulfonate</strong> (0.5 mmol) and DCC (0.9 mmol) at rt with stirring for 24 h. The reaction mixture was filtered through filter paper to remove DCU, the filtrate diluted with CH2Cl2 (50 mL), washed with DI water (3 × 50 mL), and the CH2Cl2 layer dried (Na2SO4). Filtration of Na2SO4 and removal of the solvent yielded the crude product that was purified over silica using 6:4 EtOAc/hex to afford the product.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 2048 - 2051

46
[ 42772-85-0 ]
[ 73736-50-2 ]
1-(4-fluorobenzyl)-N-(1-(4-(2-fluorobutoxy)phenethyl)piperidin-4-yl)-1H-benzo[d]imidazol-2-amine [ No CAS ]

Reference： [1]MedChemComm,2013,vol. 4,p. 852 - 855

47
[ 42772-85-0 ]
[ 1571933-53-3 ]
[ 1571933-55-5 ]

Yield	Reaction Conditions	Operation in experiment
68%	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20℃; for 3h;Cooling with ice;	Compound 6 (116 mg, 0.25 mmol) obtained in the above Example 1(5), triphenylphosphine (131 mg, 0.5 mmol) and 2-hydroxyethyl-4-methyl benzenesulfonate (108 mg, 0.5 mmol) were dissolved in anhydrous THF (2.5 mL). The solution was cooled with ice, and then diethyl azodicarboxylate (218 mg, 0.5 mmol) was added thereto. The temperature of the reaction mixture was increased to room temperature and stirred for 3 hours. Then, the reaction mixture was diluted with water, and extraction was carried out with ethyl acetate. The organic layer was washed with water and saturated saline, and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. Compound 7 was obtained by purifying from the residue with silica gel column chromatography (amount: 112 mg, yield: 68%).

Reference： [1]Patent: US2014/187814,2014,A1 .Location in patent: Paragraph 0157-0158

48
[ 42772-85-0 ]
[ 358-23-6 ]
2-[(4-methylbenzenesulfonyl)oxy]ethyl trifluoromethanesulfonate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 6473 - 6476
Angew. Chem.,2014,vol. 126,p. 6591 - 6594,4

49
[ 42772-85-0 ]
[ 383-50-6 ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 6473 - 6476
Angew. Chem.,2014,vol. 126,p. 6591 - 6594,4
[2]European Journal of Medicinal Chemistry,2014,vol. 90,p. 742 - 750

50
[ 42772-85-0 ]
[ 1517-05-1 ]

Yield	Reaction Conditions	Operation in experiment
96%	With sodium azide; In ethanol; at 70℃;	Sodium azide (0.3 g,4.65 mmol) was added to a solution of monotosylatedethylene glycol 11 (1 g, 4.2 mmol) in 5 ml ethanol, and thereaction was reBuxed overnight on 70C. )en, the reactionwas diluted with diethyl ether and washed with water threetimes. )en, the organic layers were collected and a pure paleyellow oily product was obtained after evaporation (Yield96%, 350 mg, 4.02 mmol). Rf: 0.6 (DCM/MeOH 20 : 1). 1HNMR (500 MHz, CDCl3): * 3.73 (t, 2H, J 4.1 Hz, CH2OH),3.40 (t, 2H, J 4.7 Hz, CH2N3), 2.25 (bs, 1H, OH). 13C NMR(125 MHz, CDCl3): * 61.8, 53.5.
95%	With sodium azide; In water; acetone; at 60℃; for 12h;	General procedure: In a round-bottom flask, compounds 40a-d (13.27 mmol) and sodiumazide (26.54 mmol) were dissolved in a mixed solution of acetone(5 mL) and water (5 mL). The mixture solution was heated to 60 C andstirred for 12 h. Then saturated sodium carbonate solution (5 mL) wasadded to quench the reaction, subsequently, the mixture was extractedwith ethyl acetate. The organic layer was dried over anhydrous sodiumsulfate and concentrated. The crude residue was purified by flashcolumn chromatography (petroleum ether/ethyl acetate = 30:1) togive 41a-d.
90.64%	With sodium azide; In water; acetone; for 16h;Reflux;	Dissolve 1a (2 g, 9.25 mmol) and sodium azide (1.2 g, 18.5 mmol) in 5 mL of acetone and 5 mL of water.After heating under reflux for 16 hours, 20 mL of water was added, extracted with ethyl acetate, washed with saturated aqueous sodium carbonate, and washed with saturated brine, and collected.The organic layer was dried over anhydrous sodium sulfate, and the organic solvent was evaporated under reduced pressure to obtain a colorless liquid, weighed 0.73 g, and the yield was 90.64%.

85%	With sodium azide; In water; acetone; at 60℃; for 16h;	A solution of compound 27a (1.2 g,5.55 mmol) and sodium azide (0.72 g, 11.1 mmol) of propanone/H2O(10 mL, 1/1) was heated to reflux for 16 h. The reaction mixture wasdiluted with water and extracted with EtOAc. The combined organiclayers were washed with saturated sodium carbonate solution andbrine, dried over Na2SO4, and evaporated in vacuo. The residue waspurified by column chromatography on silica gel (EtOAc/petroleumether, 1/30) to afford 28a (0.41 g, 85%) as a colorless liquid. 1H NMR(300 MHz, CDCl3) delta (ppm): 3.82-3.74 (m, 2H), 3.49-3.39 (m, 2H), 2.01(s, 1H).
84.85%	With sodium azide; In water; acetone; for 16h;Reflux;	A solution of 1a (1.2 g, 5.55 mmol) and sodium azide (0.72 g, 11.1 mmol) were dissolved in 5 mL of acetone and 5 mLWater mixture, heated to reflux for 16 hours by adding 20mL of water, extracted with ethyl acetate, saturated aqueous sodium carbonate solution, saturated salt water washing, The organic layer was dried over anhydrous sodium sulfate and the organic solvent was evaporated under reduced pressure to give a colorless liquid weighing 0.41 g in 84.85% yield.
84.85%	With sodium azide; In water; acetone; for 16h;Reflux;	Will 1a (1.2g, 5.55mmol)And sodium azide (0.72g, 11.1mmol) was dissolved in 5mL acetone and 5mL water mixture,Heated for reflux for 16 hours,Add 20 mL of water, extract with ethyl acetate, and wash with saturated aqueous sodium carbonate.The organic layer was collected and dried over anhydrous sodium sulfate.Obtained a colorless liquid weighing 0.41gThe yield was 84.85%.
84.85%	With sodium azide; In water; acetone; for 16h;Reflux;	The 1a (1.2g, 5.55mmol) and sodium azide (0.72g, 11.1mmol) was dissolved in 5mL 5mL of acetone and water mixture, was heated at reflux for 16 hours, 20mL water and extracted with ethyl acetate and saturated sodium carbonate wash solution and brine, the organic layer was collected, dried over anhydrous sodium sulfate, the organic solvent was distilled off under reduced pressure, to give a colorless liquid, weight 0.41g, 84.85% yield.
	With sodium azide; In water; at 115℃; for 20h;	The compound was prepared according to the procedure published in literature [7]. Compound 21 (11.73 g, 0.054 mmol) was suspended in H2O (30 mL) and sodium azide (4.24 g, 0.065 mmol) was added. The reaction mixture was refluxed at 115 C. After 2 h all the components of the reaction were dissolved. The reaction was complete after 20 h, which was determined by TLC (hexane/ethyl acetate 1:1). The reaction mixture was saturated by anhydrous MgSO4 and the product extracted into CH2Cl2 (3 × 10 mL), which was previously purified by distillation with P2O5 (to remove ethanol which is used as stabilizing agent). CH2Cl2 extracts were merged and dried with anhydrous MgSO4. The product was obtained as CH2Cl2 solution and wasn?t further isolated and characterized due to its potentially explosive character and was used directly in next reaction step. TLC (hexane-ethyl acetate 1:1) of the solution showed one spot with Rf = 0.5.

Reference： [1]Journal of Chemistry,2020,vol. 2020
[2]Bioorganic and Medicinal Chemistry,2020,vol. 28
[3]Patent: CN107698575,2018,A .Location in patent: Paragraph 0101-0103
[4]Bioorganic Chemistry,2020,vol. 99
[5]Patent: CN107056772,2017,A .Location in patent: Paragraph 0073; 0074; 0075; 0076
[6]Patent: CN110204543,2019,A .Location in patent: Paragraph 0097; 0104-0107
[7]Patent: CN110143961,2019,A .Location in patent: Paragraph 0092; 0099-0102
[8]Beilstein Journal of Organic Chemistry,2014,vol. 10,p. 1390 - 1396
[9]Patent: CN110420334,2019,A .Location in patent: Paragraph 0091-0092; 0097

51
[ 42772-85-0 ]
[ 55022-46-3 ]
[ 1245721-44-1 ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 3854 - 3858
Angew. Chem.,2014,vol. 126,p. 3934 - 3939,5

52
[ 5256-74-6 ]
[ 42772-85-0 ]
1,3-diethyl 2-{2-[(4-methylbenzenesulfonyl)oxy]ethoxy}propanedioate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 14230 - 14234
Angew. Chem.,2014,vol. 126,p. 14454 - 14458,5

53
[ 42772-85-0 ]
[ 1032900-25-6 ]
[ 1032900-27-8 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2016,vol. 59,p. 103 - 108

54
[ 42772-85-0 ]
1-(2'-octyl)dodecyl-2-(4'-carboxymethyl)butylglycerol [ No CAS ]
1-(2'-octyl)dodecyl-2-(4'-carboxymethyl)butyl-glycero-sn-3-phosphoric acid tosylethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
6.90 g		Procedure B l-(2'-octyl)dodecyl-2-(4'-carboxymethyl)butyl-glycero-sn-3 -phosphoric acid tosylethyl ester [0263] A solution of l-(2'-octyl)dodecyl-2-(4'-carboxymethyl)butyl-glycerol (7.47 g, dried by azeotropic distillation with benzene) and triethylamine (7 ml) in dry THF (80 ml) was added dropwise for 2 hrs at 0 C to a stirred solution of phosphorus oxychloride (2 ml) in dry THF (50 ml). The reaction mixture stirred at 0C for an additional 15 minutes and at room temperature for an additional 45 minutes. The reaction mixture was cooled again to 0 C and a solution of O-tosyl ethylene glycol (3.65 g, dried by azeotropic distillation with benzene) in dry THF (50 ml) was added dropwise for 30 min. The resulting mixture was stirred at room temperature overnight, then filtered, and the solvent removed under reduced pressure. The residue was dissolved in water (100 ml), refluxed for 1 hr, then cooled and extracted with ether (2 x 100 ml). The combined organic phase was washed with water (100 ml) and the solvent removed under reduced pressure. The residue (9.62 g) was purified by chromatography on a column of silica gel (250 g). Elution with mixtures of CHC13: MeOH (5-20%, v/v) and removal of solvent under reduced pressure yielded 6.90 g of l-(2'-octyl)dodecyl-2-(4'-carboxymethyl)butyl- glycero-sn-3 -phosphoric acid tosylethyl ester

Reference： [1]Patent: WO2016/84024,2016,A1 .Location in patent: Page/Page column 59; 60

55
[ 42772-85-0 ]
[ 1717-59-5 ]
2-(difluoromethoxy)ethyl 4-methylbenzenesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%		To a stirred solution of <strong>[42772-85-0]2-hydroxyethyl 4-methylbenzenesulfonate</strong> (5.52 g, 25.5 mmol) in acetonitrile (40 mL) was added copper (I) iodide (972 mg, 5.1 mmol). The resulting mixture was stirred at 70 C and treated with 2,2-difluoro-2-fluorosulfonyl-acetic acid as a solution in acetonitrile (5 mL) dropwise over a period of 30 mm (mixture gradually turns dark red). The resulting mixture was treated with anhydrous sodium sulfate (5 mg) and stirring continued (steady evolution of gas observed, colour fades to yellow) for a further 30 mm. The mixture was then cooled to room temperature, diluted with diethyl ether and washed with brine (lx), a 1:1 mixture of brine:water (2x) and brine (lx). The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo then chromatographed in 0-20 % ethyl acetate in hexanes. The product containing fractions were concentrated in vacuo giving the desired product as a clear liquid (4.2 g, 62%). 1H NMR (d6-DMSO) O 7.78 (d, J = 9 Hz, 2H), 7.48 (d, J = 9 Hz, 1H), 6.63 (t, J = 75Hz, 1H), 4.21-4.14 (m, 2H), 4.02-3.96 (m, 2H), 2.41 (s, 3H).
62%		[00181 ] To a stirred solution of 2-hydroxyethyl 4- methylbenzenesulfonate (5.52 g, 25.5 mmol) in acetonitrile (40 mL) was added copper (I) iodide (972 mg, 5.1 mmol). The resulting mixture was stirred at 70 C and treated with 2,2-difluoro-2-fluorosulfonyl-acetic acid as a solution in acetonitrile (5 mL) dropwise over a period of 30 min (mixture gradually turns dark red). The resulting mixture was treated with anhydrous sodium sulfate (5 mg) and stirring continued (steady evolution of gas observed, colour fades to yellow) for a further 30 min. The mixture was then cooled to room temperature, diluted with diethyl ether and washed with brine (1x), a 1 : 1 mixture of brine:water (2x) and brine (1x). The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo then chromatographed in 0 - 20 % ethyl acetate in hexanes. The product containing fractions were concentrated in vacuo giving the desired product as a clear liquid (4.2 g, 62%).

Reference： [1]Patent: WO2016/123706,2016,A1 .Location in patent: Paragraph 00227
[2]Patent: WO2016/123707,2016,A1 .Location in patent: Paragraph 00180; 00181

56
[ 42772-85-0 ]
[ 2009-97-4 ]
(±)-ethyl 3-oxo-2-(2-(tosyloxy)ethoxy)butanoate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 11477 - 11488

57
[ 42772-85-0 ]
[ 1616922-83-8 ]
2-(tosyloxy)ethyl 5-(benzyloxy)-6-hydroxy-2-((1-phenylcyclopentyl)methyl)pyrimidine-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75.3%		To a solution of 5-(benzyloxy)-6-hydroxy-2-((1-phenylcyclopentyl)methyl)pyrimidine-4- carboxylic acid intermediate (CAS 1616922-83-8 , prepared according to US 20140194431 , 1.5 g, 3.71 mmol) and DIPEA (1.29 mL, 7.42 mmol) in anhydrous DCM (40 mL) was added HATU (1.7 g, 4.45 mmol). The mixture was stirred at 0 C for 0.5 h, then 2-hydroxyethyl 4- methylbenzenesulfonate (882 mg, 4.08 mmol) was added and stirred for 16 h. After completion of the reaction, the reaction mixture was concentrated under vacuum and purified by column chromatography on silica gel eluted PE/EA = 5/1 to 2/1 to provide the title compound (1.68 g, 75.3%) as a white solid. (1306) MS (ESI, m/z): 603.2 [(M+Hf]

Reference： [1]Patent: WO2017/158151,2017,A1 .Location in patent: Page/Page column 209

58
[ 100-02-7 ]
[ 42772-85-0 ]
[ 16365-27-8 ]

Reference： [1]RSC Advances,2017,vol. 7,p. 22388 - 22399

59
[ 42772-85-0 ]
C₂₁H₂₄N₂O₃ [ No CAS ]
N-((3s,5s,7s)-adamantan-1-yl)-1-(2-hydroxyethyl)-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23%	With caesium carbonate; In N,N-dimethyl-formamide; at 90℃; for 3h;	To a solution of 1 (200 mg, 0.567 mmol) in DMF (4 mL), <strong>[42772-85-0]2-hydroxyethyl 4-methylbenzenesulfonate</strong> (183 mg, 0.847 mmol)and Cs2CO3 (276 mg, 0.847 mmol) were added. The reactionmixturewas stirred at 90 C for 3 h, subsequently poured intowater(100 mL) and extracted 3 times with DCM (20 mL). The organiclayers were combined, dried over MgSO4 and evaporated underreduced pressure. The crude residue was chromatographed usingpure EtOAc to give the title compound (52 mg, 0.131 mmol, 23%yield). 1H NMR (400 MHz, CDCl3): d 10.0 (s, 1H), 8.7 (s, 1H), 8.1 (dd,J 8.1, 1.4 Hz, 1H), 7.4 (t, J 8.1 Hz, 1H), 7.2 (d, J 7.7 Hz, 1H), 4.8 (t,J 4.9 Hz, 2H), 4.0 (t, J 4.9 Hz, 2H), 4.0 (s, 3H), 3.8 (s, 1H), 2.0e2.1(m, 9H), 1.7e1.8 (m, 6H). 13C NMR (100 MHz, CDCl3): d 176.2, 164.0,151.1, 150.0, 130.7, 130.2, 125.3, 119.6, 114.5, 111.9, 62.2, 61.9, 56.6,51.8, 41.9, 36.7, 29.7. HRMS calculated for C23H29N2O4 [MH]397.2122, found 397.2122.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 145,p. 746 - 759

60
[ 42772-85-0 ]
C₂₈H₃₆ClFN₄O₆ [ No CAS ]
C₃₀H₄₀ClFN₄O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With sodium hydride; In tetrahydrofuran; at 40℃; for 5h;Cooling with ice;	In an ice water bath, compound c (1.2 g, 2 mmol) was1-1 (0.43 g, 2 mmol) was added to tetrahydrofuran (30 mL),Sodium hydride (0.15 g, 6.3 mmol) was slowly added to the reaction solution.The reaction solution was heated to 40C and stirring was continued for 5 hours. The reaction was quenched by adding 5 ml of water slowly.The organic solvent was distilled off under reduced pressure and water (100 mL) and dichloromethane (100 mL) were added.Stir and stand and collect the organic phase. The organic phase is dried over anhydrous sodium sulfate and distilled under reduced pressure.The crude product was purified by chromatography on a silica gel column eluted with chloroform/methanol (10:1).A brown solid was obtained as compound 1-2 (0.78 g, 63%).

Reference： [1]Patent: CN107474065,2017,A .Location in patent: Paragraph 0070; 0071; 0076; 0077

61
[ 42772-85-0 ]
1-[1-(5-oxo-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethyl]-1H-imidazole-5-carboxylic acid [ No CAS ]
C₂₇H₂₉N₃O₆S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%		Compound 11 (150 mg, 0.461 mmol) obtained by the method shown in Step 6 - 1 was dissolved in dichloromethane (10 mL)4-dimethylaminopyridine (5.6 mg, 0.0461 mmol),Triethylamine (0.193 mL, 1.38 mmol) was added. Under ice-cooling, 2-methyl-6-nitrobenzoic anhydride (238 mg,0.692 mmol) was added,The mixture was stirred at 0 C. for 20 minutes under an argon atmosphere.below freezing,Compound 18 (199 mg, 0.922 mmol) obtained in Step 8 - 1 was added, and under an argon atmosphere,And the mixture was stirred at 0 C. for 1.5 hours.After completion of the reaction, the reaction solution was concentrated under reduced pressure,The obtained crude product was purified by silica gel column chromatography (eluent (volume ratio): ethyl acetate - ethyl acetate / methanol = 50/1) to obtain Compound 19 (182 mg, 0.348 mmol, yield 75% ) Was obtained.

Reference： [1]Patent: JP2015/110563,2015,A .Location in patent: Paragraph 0016; 0082; 0084

62
crizotinib [ No CAS ]
[ 42772-85-0 ]
3-((R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(1-(hydroxyethylpiperidin-4-yl)-1H-pyrazol-4-yl)pyridin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With triethylamine; In acetonitrile; at 95℃; for 5h;	3-((R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)pyridin-2-amine (crizotinib; 50 mg,0.11 mmol) was dissolved in dry MeCN (2.0 mL), and then triethylamine(0.6 mL, excess) was added. To this mixture, ethyleneglycolmonotosylate (48 mg, 0.2 mmol, 2.0 eq.) was added, andthe mixture was refluxed at 95 C for 5 h. The reaction mixture wasconcentrated under vacuum, and the crude product was purified byflash chromatography on silica gel, eluted with 100% EtOAc toremove unreacted ethylene glycol monotosylate, and then elutedwith 10% MeOH/CH2Cl2. After solvent evaporation, hydroxyethylcrizotinib (compound 2) was obtained as an off-white solid (40 mg,74% yield) with 95% purity. 2: Rf 0.4 in 10% MeOH/CH2Cl2; 1HNMR (CDCl3, 500 MHz), d: 7.76 (s, 1H), 7.56 (s, 1H), 7.50 (s, 1H), 7.30(m, 1H), 7.05 (t, J 8.0 Hz, 1H), 6.87 (s, 1H), 6.07 (q, J 6.6 Hz, 1H),4.79 (s, 2H, NH2), 4.14 (m, J 4.3 Hz, 1H), 3.65 (t, J 4.8 Hz, 2H), 3.07(d, J 10.9 Hz, 2H), 2.60 (t, J 4.8 Hz, 2H), 2.28 (t, J 11.7 Hz, 2H),2.17 (d, J 11.4 Hz, 2H), 2.06 (q, J 11.9 Hz, 2H), 1.85 (d, J 6.5 Hz,3H). 13C NMR decoupled (CDCl3,125 MHz), d: 148.89,139.85,136.95,135.72, 135.51, 128.96, 128.93, 122.58, 122.13, 121.93, 119.93, 119.21,116.81, 116.63, 114.96, 72.42, 59.32, 59.07, 58.01, 52.32, 32.54, 18.90.MS: m/z [MH] 494.88.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 182

63
[ 42772-85-0 ]
[ 18162-48-6 ]
[ 148400-72-0 ]

Yield	Reaction Conditions	Operation in experiment
79%	With triethylamine; In dichloromethane; at 0 - 20℃; for 23.17h;	t-Butyldimethylsilylethyl tosylate was prepared as describedpreviously [54] with modification. Briefly, hydroxyethyl tosylate(200 mg, 0.924 mmol, 1.0 eq.) and t-butyldimethylsilyl chloride(418 mg, 2.774 mmol, 3.0 eq.) were dissolved in CH2Cl2 (8 mL).Then, triethylamine (0.64 mL, 4.624 mmol, 5.0 eq.) was added at0 C, and the resulting mixture was stirred for 10 min. The mixturewas then warmed to room temperature and stirred for 23 h. Thereaction mixture was washed with water (2 5 mL), and theaqueous layer was extracted with CH2Cl2. Combined organic layerswere dried over MgSO4, filtered, and evaporated. The crude productwas purified by flash column chromatography on silica gel using 12% EtOAc/Hex to obtain t-butyldimethylsilylethyl tosylate as a paleyellow oil (243 mg, 79% yield) with 95% purity. The compound wasfully characterized by 1H NMR spectroscopy and MS. Rf 0.9 in 50%EtOAc/Hex; 1H NMR (CDCl3, 600 MHz) d: 7.79 (d, J 8.2 Hz, 2H),7.32 (d, J 8.1 Hz, 2H), 4.06 (t, J 4.9 Hz, 2H), 3.79 (t, J 5.2 Hz, 2H),2.44 (s, 3H), 0.83 (s, 9H), 0.016 (s, 6H). MS: m/z [MH] 331.13. Thecompound's NMR spectrum was consistent with that reportedpreviously [55].

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 182

64
[ 42772-85-0 ]
[ 1201808-21-0 ]
2-(2, 2-diphenylbenzo[d][1, 3]dioxol-5-yl)-5-hydroxy-7-(2-hydroxyethoxy)-4H-chromen-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With potassium carbonate; In acetonitrile;Reflux;	Potassium carbonate (143 mg, 1.0 mmol) was added to a solution of 14 (310 mg, 0.7 mmol) and 15a (223 mg, 1.0 mmol) in CH3CN (4 mL) at room temperature. The reaction mixture was then refluxed overnight. The resulting mixture was poured into ice-water, adjusted to neutral PH with aqueous HCl (5%), and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (CH2Cl2/acetone = 10:1) to give 16a as yellow solid (195 mg, 57%). 1HNMR (CDCl3, 400MHz) delta 3.99 (2H, t, J = 4.0Hz, -OCH2-), 4.13 (2H, t, J = 4.0Hz, -OCH2-), 6.34 (1H, d, J = 1.6Hz, H-6), 6.45 (1H, d, J = 1.6Hz, H-8), 6.50 (1H, s, H-3), 6.96 (1H, d, J = 8.0Hz, H-6?), 7.34-7.46 (8H, m, H of diphenylmethane, H-2?,H-5?), 7.54-7.63 (4H, m, H of diphenylmethane); 13CNMR (CDCl3, 100MHz) delta 182.29, 164.42, 163.77, 162.09, 157.51, 150.37, 148.03, 139.47, 129.42, 128.37 (5C), 126.17 (5C), 125.13, 121.58, 118.35, 108.91, 106.41, 105.69, 104.69, 98.52, 93.00, 69.79, 61.07. MS (ESI) m/z: 495.1 (M + H)+.
57%	With potassium carbonate; In acetonitrile;Reflux;	General procedure: Potassiumcarbonate (143 mg, 1.0 mmol) was added to a solution of 23 (315 mg, 0.7 mmol) and TsO(CH2)3OH(230 mg, 1.0 mmol) in CH3CN (4 mL) at room temperature. The reaction mixture was then refluxedovernight. The resulting mixture was poured into ice-water, adjusted to neutral pH with aqueousHCl (5%), and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4,filtered, and concentrated in vacuo. The residue was purified by column chromatography (petroleumether/acetone = 5:1) to give 25a as yellow solid (218 mg, 34.2%).

Reference： [1]Bioorganic Chemistry,2019,vol. 92
[2]Molecules,2020,vol. 25

65
[ 42772-85-0 ]
[ 69-72-7 ]
[ 55211-84-2 ]

Reference： [1]Journal of Enzyme Inhibition and Medicinal Chemistry,2020,vol. 35,p. 152 - 164

66
[ 42772-85-0 ]
[ 99-06-9 ]
[ 25781-99-1 ]

Reference： [1]Journal of Enzyme Inhibition and Medicinal Chemistry,2020,vol. 35,p. 152 - 164

67
[ 42772-85-0 ]
[ 99-96-7 ]
[ 1711-24-6 ]

Reference： [1]Journal of Enzyme Inhibition and Medicinal Chemistry,2020,vol. 35,p. 152 - 164

68
[ 42772-85-0 ]
[ 53555-73-0 ]
2-(4-((4-methoxyphenyl)(pyridin-2-yl)methyl)phenoxy)ethanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%		General procedure: To a solution of compound 3 (1 equiv) in anhydrous DMF (8 mL)was added K2CO3 (4 equiv). The mixture was stirred at 80 C for 1 h,under argon. Then a solution of the corresponding glycol mono-tosylate(1 equiv, except for 4a, 3 equiv) in dry DMF (2 mL) was added dropwiseand the mixture was stirred at 80 C (monitoring by TLC). After reactioncompletion, the reaction mixture was diluted with water (80 mL) andextracted with CH2Cl2 (5×80 mL). The organic layer was washed witha saturated solution of NaHCO3 (3 × 80 mL), brine (3 × 80 mL) andwater (3 × 80 mL), and then dried over MgSO4. The solvent was removedin vacuo and then the product was purified by flash columnchromatography on silica gel to afford the corresponding PEGylatednon-symmetrical triarylmethanes 4a-e Yields: 4a, 72% ; 4b, 40% ; 4c,40% ; 4d, 33% ; 4e, 69%.4.2.1.1. 2-(4-((4-methoxyphenyl)(pyridin-2-yl)methyl)phenoxy)ethanol4a. From compound 3 (0.58 mmol; 169 mg) and ethylene glycol monotosylate(1.74 mmol ; 376 mg) Reaction time: 7 days. FCC: (EtOAc/CH2Cl2, 25:75) to afford the desired compound 4a as an oil in 72% yield(141 mg). TLC (EtOAc/CH2Cl2 40:60, Rf : 0.22); IR (ATR) (cm-1): nu 751 ; 808 ; 1031 ; 1088 ; 1175 ; 1242 (nuCeOeC) ; 1464 (nuC-OH) ; 1507 ;1608 (nuC=C) ; 2931 (nuO-Me) ; 3394 (nuO-H) ; LRMS(ESI- CV = 30, 35):336.17 (M-H+) ; 358.17 (M-Na+). 1HNMR (DMSO-d6, 400 MHz)delta(ppm)=3.69 (m, 5H, H13+H21) ; 3.93 (t, 2H, H20, J=5.0 Hz) ; 4.85(br, 1H, HOH) ; 5.54 (s, 1H, H6) ; 6.85 (m, 4H, H9 + H11+ H16 +H18) ;7.09 (m, 4H, H8 + H12 + H15 + H19) ; 7.21 (m, 2H, H2 + H4) ; 7.71(ddd, 1H, H3, J = 1.9, 7.7 and 9.6 Hz) ; 8.54 (ddd, 1H, H1, J = 0.9, 1.8and 4.6 Hz); 13C NMR (DMSO-d6, 100 MHz) delta(ppm) = 55.0 (C13) ;56.5 (C6) ; 59.6 (C20) ; 69.4 (C21) ; 113.6 (C9+C11) ; 114.2 (C16 +C18); 121.5 (C2 or C4) ; 123.4 (C2 or C4) ; 129.9 (C8 + C12 + C15 + C19) ;135.3 (C7 or C14) ; 135.4 (C7 or C14) ; 136.7 (C3) ; 149.1 (C1) ; 157.1(C17) ; 157.6 (C10) ; 163.1 (C5). HRMS: calcd. for C21H21NO3H(336.1594); found (336.1596).

Reference： [1]Bioorganic Chemistry,2020,vol. 96

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H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 42772-85-0 ]

Quality Control of [ 42772-85-0 ]

Related Doc. of [ 42772-85-0 ]

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[ 42772-85-0 ] Synthesis Path-Upstream 1~2

[ 42772-85-0 ] Synthesis Path-Downstream 1~68

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