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Influence of the O3 protecting group on stereoselectivity in the preparation of C-mannopyranosides with 4,6-O-benzylidene protected donors.

ABSTRACT: ?-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.

SUBMITTER: Crich D

PROVIDER: S-EPMC3064765 | biostudies-literature | 2010 Dec

REPOSITORIES: biostudies-literature

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Influence of the O3 protecting group on stereoselectivity in the preparation of C-mannopyranosides with 4,6-O-benzylidene protected donors.

Crich David D Sharma Indrajeet I

The Journal of organic chemistry 20101111 24

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. ...[more]

PMID: 21070063

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