Pyridine → methyl 2,3,4-tri-O-benzyl-6-O-trifluoromethylsulfonyl-alpha-D-glucopyranoside

Participants

Reaction Conditions

Reaction Steps

To a solution of dry pyridine (0.46 mL) in methylene chloride (17.5 mL) cooled to -15° C. was added trifluoromethanesulfonic anhydride (0.87 mL). The mixture was stirred during 15 min at -10° C., then methyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside (1.2 g, 2.58 mmol) in methylene chloride (5 mL) was added [P. Kovac, V. Sklenar and C. Glaudemans, Carbohydr. Res. 175, 201 (1988)]. The mixture was stirred during 1.5 h at -10° C. The reaction mixture was washed with water. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to afford an oil. Flash chromatography on silica gel and elution with a 7:3 mixture of hexane and ethyl acetate afforded the expected compound methyl 2,3,4-tri-O-benzyl-6-O-trifluoromethylsulfonyl-α-D-glucopyranoside which was crystallized from hexane (1.43 g, 93%); m.p. 44°-45° C.

Provenance & Evidence