Methanol → HCID 23396148, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of sodium hydride (196 mg, 5.1 mmol) in dry DMF (10 mL) was cooled to 0° C., and a solution of methyl 2-azido-6-O-tert-butyldiphenylsilyl-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D glucopyranoside (10) (2.53 g, 4.3 mmol) in dry DMF (20 mL) was added dropwise in 30 minutes. The resulting solution was stirred at room temperature for 30 minutes and benzyl bromide (880 mg, 5.1 mmol) was added dropwise at 0° C. The reaction mixture was stirred at room temperature overnight, cooled to 0° C. and dry methanol (1 mL) was added dropwise. The reaction mixture was concentrated under reduced pressure, then xylene (20 mL) was co-evaporated from the residue. The residue was taken up in CHCl3 (100 mL) washed with H2O (100 ml), saturated NaHCO2 solution (100 mL) dried over MgSO4 and evaporated to dryness. The residue was purified by chromatography using EtOAc—Hexane 1:9 as the mobile phase to give methyl 2-azido-4-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside (32) (2.0 g, 68%).

Provenance & Evidence