The synthetic route of 28244-94-2 has been constantly updated, and we look forward to future research findings.
With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.28244-94-2,4-Methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-¦Â-D-glucopyranoside,as a common compound, the synthetic route is as follows.
1,2,3,4,6-Penta-O-acetyl-D-glucopyranose S1 (10.0 g, 0.0267 mol) and p-thiocresol (4.0 g, 0.032 mol) was dissolved in CH2Cl2(100mL) in a flame dried flask under nitrogen atmosphere. Boron trifluoride diethyl etherate (5.60 mL, 0.04mol) was slowly added at 0 C. After stirring for 16 hours at room temperature, the reaction mixture was diluted with CH2Cl2(100mL), washed with NaHCO3 (100 mL ¡Á 2) and brine (100 mL), dried over anhydrous MgSO4, filtered, and then concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel (EtOAc/Hexane = 0/1 to 1/2) to obtain 2,3,4-tri-O-acetyl-1-thio-beta-Dglucopyranoside S2.To a solution of compound S2 in methanol (100 mL) was added sodium methoxide (432.0 mg, 0.008mol) at room temperature under ambient atmosphere. After stirring for 4 hours, amberlite IR (120 H+) acid resin was added protionwise until the solution was neutralized. The mixture was filtered, concentrated under reduced pressure, and then volatiles were removed in vacuo to afford tetrol glycosideS3. To a solution of tetrol glucopyranoside S3 and benzaldehyde dimethyl acetal(6.10 g, 0.040 mol) in dried acetonitrile (100 mL) was added camphorsulfonic acid (0.620 g, 2.670 mmol) in a flame dried flask under nitrogen atmosphere. After stirring for 6 hours at room temperature, the reaction solution was diluted with ethyl acetate (100 mL), washed with NaHCO3 (50 mL ¡Á 2) and brine (50 mL), dried over anhydrous MgSO4, filtered, concentrated under reduced pressure, and then volatileswere removed in vacuo to obtain 4,6-O-benzylidine-D-glucopyranoside S4.To a solution of 4,6-O-benzylidine-D-glucopyranoside S4 in dried DMF (80 mL) was added benzyl bromide (7.0 mL, 0.059 mol) in a flame dried flask under nitrogen atmosphere. Sodium hydride (60% dispersion in mineral oil, 2.560 g, 0.064mol) was added portionwise and gradually in the reaction solution at 0 C. After s20stirring for 16 hours at room temperature, the mixture was diluted with ethyl acetate (100 mL), quenched by water (50 mL¡Á2) and washed with brine (50 mL), dried over anhydrous MgSO4, filtered, and then concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel (EtOAc/ Hexane= 0/1 to 1/4) and then volatiles were removed in vacuo to acquire the benzyl glycoside S5 as a white solid.Compound S5 was dissolved in dried CH2Cl2(50 mL) in a flame dried flaskunder nitrogen atmosphere. Borane-tetrahydrofurane complex (1M in THF, 130 mL, 0.13 mol) and trimethyl silyltrifluoromethanesulfonate (2.30 mL, 0.013 mol) was added subsequently in the reaction solution at 0 C After stirring for 6 hours at 0oC, the reaction mixture was quenched by NaHCO3 (50 mL¡Á3), washed with brine (50 mL), dried over anhydrous MgSO4, filtered, and then concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel (EtOAc/ Hexane= 0/1 to 1/2) and then volatiles were removed in vacuo to acquire the product (64) as white solid. [alpha]28D4.93 (c 0.58, CHCl3); 1H NMR (400 MHz, CDCl3) delta 7.42-7.27 (m, 17 H, Ph), 7.11 (d, J8.0 Hz, 2 H, Ph), 4.93- 4.83 (m, 3 H, PhCH), 4.76 (d, J10.4 Hz, 1 H, PhCH), 4.61 (d, J12.4 Hz, 2 H, PhCH and H-1), 3.89-3.83 (m, 1 H, H-6), 3.71 (t, J9.2 Hz, 1 H, H-3), 3.70-3.65 (m, 1 H, H-6), 3.55 (t, J9.2 Hz, 1 H, H-4), 3.45 (t, J9.2 Hz, 1 H, H-2),3.38-3.33 (m, 1 H, H-5), 2.33 (s, 3 H, Me), 1.89 (t, J6.8 Hz, 1 H, OH) ppm; 13C NMR: delta 138.3-137.8 (C), 132.5 (CH), 129.7 (CH), 129.4 (CH), 128.4-127.6 (CH), 87.7 (CH), 86.5 (CH), 81.0 (CH), 79.2 (CH), 77.6 (CH), 75.6 (CH2), 75.3 (CH2), 75.0 (CH2), 62.0 (CH2), 20.9 (CH3) ppm; HRMS (ESI, m/z) calcd for C34H36O5NaS [M + Na]+requires 579.2181, found 579.2183, 28244-94-2
The synthetic route of 28244-94-2 has been constantly updated, and we look forward to future research findings.
Reference£º
Article; Hsu, Mei-Yuan; Liu, Yi-Pei; Lam, Sarah; Lin, Su-Ching; Wang, Cheng-Chung; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 1758 – 1764;,
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