Triethylamine → (3E)-4-[3-methyl-4-({5-(propan-2-yl)-3-[(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)oxy]-1H-pyrazol-4-yl}methyl)phenyl]but-3-en-1-yl methanesulfonate

Participants

Reaction Steps

Add methanesulfonyl chloride (1.35 g, 11.8 mmol) to a solution of 4-{4-[(1E)-4-hydroxybut-1-en-1-yl]-2-methylbenzyl}-5-(propan-2-yl)-1H-pyrazol-3-yl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside (1.5 g, 2.38 mmol) and triethylamine (5 g, 49.2 mmol) in dichloromethane (50 mL) at 0° C. After 30 minutes at room temperature, extract with dichloromethane (80 mL), and wash with water (80 mL) and brine (40 mL). Dry organic phase over sodium sulfate, filter and concentrate under reduced pressure. Purify the resulting residue by flash chromatography (silica gel, gradient ethyl acetate/dichloromethane from 10-65% over 20 min, 120 g column) to yield the title compound (5.4 g, 7.62 mmol). MS (m/z): 708.5 (M+1), 706.5 (M−1).

Provenance & Evidence