tert-Butyldiphenylchlorosilane → HCID 12114344, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of t-butyldiphenylsilyl chloride (8.66 g, 31.53 mmol), 4-dimethylaminopyridine (5.12 g, 42.04 mmol) and methyl 2-azido-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside (9) (7.21 g, 21.02 mmol) in dry 1,2-dichloroethane (100 mL) was stirred at 80° C. for 2 hours. The resulting clear solution was cooled to room temperature, diluted with CHCl3 (300 mL), washed with H2O (3×200 mL), brine solution (200 mL), dried over MgSO4 and evaporated. The residue was purified by chromatography using hexane—ether 2:1 as the mobile phase to give methyl 2 -azido-6-O-tert-butyldiphenylsilyl-2-deoxy-3-O-(4-methoxybenzyl-1-thio-β-D glucopyranoside (10) (9.73 g, 80%).

Provenance & Evidence