Influence of the O3 Protecting Group on Stereoselectivity in the Preparation ofC-Mannopyranosides with 4,6-O-Benzylidene Protected Donors
- 11 November 2010
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 75 (24) , 8383-8391
- https://doi.org/10.1021/jo101453y
Abstract
α-C-Glucopyranosides and mannopyranosides are obtained in 65−85% yields from 4,6-O-benzylidene-protected glucosyl and mannosyl thioglycosides bearing ester functionality at the 3-O-position by a coupling reaction with C-nucleophiles on activation with diphenyl sulfoxide, 2,4,6-tri-tert-butylpyrimidine, and trifluoromethanesulfonic anhydride.Keywords
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