HCID 12114350, compound → HCID 23396152, compound

Participants

Reaction Steps

A mixture of methyl 2-azido-6-O-tert-butyldiphenylsilyl-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D-galactopyranoside (16) (213 mg, 0.36 mmol), 4-dimethylaminopyridine (67 mg, 0.55 mmol) in dry 1,2-dichloroethane (10 mL) was stirred at room temperature. Biphenylcarbonyl chloride (119 mg, 0.55 mmol) was added to the stirred reaction mixture. The resulting suspension was stirred under reflux for 3 hours. The reaction mixture was cooled to 10° C. and filtered. The crystalline solid was washed on the funnel with dry 1,2-dichloroethane (5 mL) and filtered. The filtrates were combined, diluted with CHCl3 (20 mL) and washed twice with diluted brine solution (water-brine 2:1) (15 mL). The organic layer was dried over MgSO4 and evaporated. The residue was purified by chromatography using hexane—CHCl3 1:1 as the mobile phase to give methyl 2-azido-6-O-tert-butyldiphenylsilyl-4-O-biphenylcarbonyl-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D-galactopyranoside (17) (18mg, 65%).

Provenance & Evidence