2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 90775216, compound

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Reaction Steps

A mixture of methyl 2-azido-4-O-benzyl-6-O-(4-chlorobenzyl)-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D glucopyranoside (34) (580 mg, 1.01 mmol) and DDQ (270 mg, 1.2 mmol) in CH2Cl2—H2O 9:1 (10 mL) was stirred at room temperature for 3 hours. The reaction mixture was washed with saturated NaHCO3 solution (3×15 ml), dried over MgSO4 and evaporated. The residue was purified by chromatography using CHCl3-Hexane-MeOH 30:20:0.5 as the mobile phase to give methyl 2-azido-4-O-benzyl-6-O-(4-chlorobenzyl)-2-deoxy-1-thio-β-D glucopyranoside (35) (300 mg, 66%).

Provenance & Evidence