HCID 12114344, compound → HCID 23396150, compound

Participants

Reaction Steps

A mixture of methyl 2-azido-6-O-tert-butyldiphenylsilyl-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D glucopyranoside (10) (12.7 g, 21.46 mmol), 4-dimethylaminopyridine (5.23 g, 42.92 mmol) in dry 1,2-dichloroethane (100 mL) was stirred at room temperature. Biphenylcarbonyl chloride (6.97 g, 32.19 mmol) was added to the stirred reaction mixture in 15 minutes. After the addition 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 (50 mL) and filtered. The filtrates were combined, diluted with CHCl3 (200 mL) and washed twice with diluted brine solution (water-brine 2:1) (150 mL). The organic layer was dried over MgSO4 and evaporated. The residue was crystallized from EtOH (75 mL) to give methyl 2-azido-6-O-tert-butyldiphenylsilyl-4-O-biphenylcarbonyl-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside (11) (12.7 g, 76%)

Provenance & Evidence