2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 23396149, compound

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Reaction Steps

A mixture of methyl 2-azido-4-O-biphenylcarbonyl-6-O-tert-butyldiphenylsilyl-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-62-D-glucopyranoside (11) (150 mg, 0.19 mmol) and DDQ (52 mg, 0.23 mmol) in CH2Cl2—H2O 9:1 (5 mL) was stirred at room temperature for 3 hours. The reaction mixture was washed with saturated NaHCO3 solution (3×3 ml), dried over MgSO4 and evaporated. The residue was purified by chromatography using EtOAc—hexane 15:85 as the mobile phase to give methyl 2-azido-4-O-biphenylcarbonyl-6-O-tert-butyldiphenylsilyl-2-deoxy-1-thio-β-D-glucopyranoside (41) (116 mg, 92%).

Provenance & Evidence