tert-Butyldiphenylchlorosilane → HCID 12114350, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of t-butyldiphenylsilyl chloride (151 mg, 0.54 mmol), 4-dimethylaminopyridine (90 mg, 0.73 mmol) and methyl 2-azido-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D-galactopyranoside (15) (130 mg, 0.36 mmol) in dry 1,2-dichloroethane (8 mL) was stirred at 80° C. for 2 hours. The resulting clear solution was cooled to room temperature, diluted with CHCl3 (20 mL), washed with H2O (3×20 mL), brine solution (20 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-galactopyranoside (16) (142 mg, 68%).

Provenance & Evidence