Acetyl chloride → [(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[[4-[2-(cyclopropoxy)ethoxy]phenyl]methyl]phenyl]-6-methoxy-tetrahydropyran-2-yl]methanol

Crude [[(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[[4-[2-(cyclopropoxy)ethoxy]phenyl]methyl]phenyl]-6-methoxy-tetrahydropyran-2-yl]methoxy]tert-butyl-dimethyl-silane 1c (4.26 g, 4.92 mmol) was dissolved in 30 mL methanol, followed by addition of acetyl chloride (52 μL, 0.74 mmol). The reaction mixture was stirred for 1 hour. The reaction mixture was concentrated under reduced pressure and purified by silica gel chromatography with elution system B to obtain the title compound [(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[[4-[2-(cyclopropoxy)ethoxy]phenyl]methyl]phenyl]-6-methoxy-tetrahydropyran-2-yl]methanol 1d (2.3 g, yellow grease), yield: 62.2%. 1H NMR (400 MHz, CDCl3): δ 7.35 (m, 13H), 7.20 (m, 3H), 7.03 (m, 4H), 6.80 (d, 2H), 4.92 (m, 3H), 4.70 (m, 1H), 4.50 (m, 1H), 4.17 (m, 1H), 4.05 (m, 3H), 3.85 (m, 6H), 3.70 (m, 2H), 3.40 (m, 1H), 3.30 (m, 1H), 3.07 (s, 3H), 0.63 (m, 2H), 0.48 (m, 2H).

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. custompurified by silica gel chromatography with elution system B

ORD 기록

ord-8a3e765f5c7b4797948c8123a414dcd3

출처 데이터셋

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08609622B2