Methyl triflate → HCID 23396146, compound

Participants

Reaction Steps

A mixture of methyl 2-azido-4-O-biphenylcarbonyl-6-O-tert-butyldiphenylsilyl-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside (11) (200 mg, 0.26 mmol), 3,4-methylenedioxybenzyl alcohol 59 mg, 0.39 mmol), molecular sieves 4A (1 g) and methyltriflate (106 mg, 0.65 mmol) in 1,2-dichloroethane (10 mL) was stirred at room temperature overnight. The reaction mixture was neutralized with TEA (0.5 mL) and evaporated. The residue was purified by chromatography using EtOAc—hexane 15:85 as the mobile phase to give 3,4-methylenedioxybenzyl 2-azido-4-O-biphenylcarbonyl-6-O-tert-butyldiphenylsilyl-2-deoxy-3-O-(4-methoxybenzyl)-α,β-D-glucopyranoside (43) (173 mg, 76%).

Provenance & Evidence