The Reaction of 2,3,4-Thi-O-Bknzyl-D-Glucose with Diethylaminosulfur Trifluoride (Dast)
Title:
The Reaction of 2,3,4-Thi-O-Bknzyl-D-Glucose with Diethylaminosulfur Trifluoride (Dast)
Author:
Kova, Pavol Yeh, Herman J. C. Jung, Grace L.
Appeared in:
Journal of carbohydrate chemistry
Paging:
Volume 6 (1987) nr. 3 pages 423-439
Year:
1987-09-01
Contents:
Treatment of 2,3,4-tri-O-benzyl-d-glucose (1) with diethylaminosulfur trifluoride (DAST) yielded 3,6-anhydro-2,4-di-O-benzyl-β-d-glucopyranosyl fluoride (11) as the main product (44%), by way of 3-benzyloxy group participation in the displacement of the intermediate 6-sulfoxo derivative. The desired 6-deoxy-6-fluoro-2,3,4-tri-O-benzyl-α- (2) and -β-d-gluco-pyranosyl fluoride (3) were formed in a combined yield of <20%. The combined yield of 2 and 3 could be increased three-fold by conducting the reaction in the presence of triethylamine.