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Stereocontrolled synthesis of D- and L-beta-rhamnopyranosides with 4-O-6-S-alpha-cyanobenzylidene-protected 6-thiorhamnopyranosyl thioglycosides.

ABSTRACT: The synthesis of both enantiomers of a 4-O-6-S-alpha-cyanobenzylidene-protected 6-thiorhamnopyranosyl thioglycoside is described starting from D-mannnose and L-arabinose derivatives for the D- and L-series, respectively. This donor is effective in the preparation of the corresponding beta-glycosides using the 1-benzenesulfinyl piperidine/trifluoromethanesulfonic anhydride protocol. Following desulfurization and concomitant debenzylation with Raney nickel, the so-formed 6-thio-beta-mannosides are converted in high yield to the beta-rhamnopyranosides.

SUBMITTER: Crich D

PROVIDER: S-EPMC2696688 | biostudies-literature | 2009 Jan

REPOSITORIES: biostudies-literature

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Stereocontrolled synthesis of D- and L-beta-rhamnopyranosides with 4-O-6-S-alpha-cyanobenzylidene-protected 6-thiorhamnopyranosyl thioglycosides.

Crich David D Li Linfeng L

The Journal of organic chemistry 20090101 2

The synthesis of both enantiomers of a 4-O-6-S-alpha-cyanobenzylidene-protected 6-thiorhamnopyranosyl thioglycoside is described starting from D-mannnose and L-arabinose derivatives for the D- and L-series, respectively. This donor is effective in the preparation of the corresponding beta-glycosides using the 1-benzenesulfinyl piperidine/trifluoromethanesulfonic anhydride protocol. Following desulfurization and concomitant debenzylation with Raney nickel, the so-formed 6-thio-beta-mannosides are ...[more]

PMID: 19132946

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