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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.

journal of organic chemistry

Stereocontrolled Synthesis of <scp>d</scp>- and <scp>l</scp>-β-Rhamnopyranosides with 4-<i>O</i>-6-<i>S</i>-α-Cyanobenzylidene-Protected 6-Thiorhamnopyranosyl Thioglycosides

Stereocontrolled Synthesis of d- and l-β-Rhamnopyranosides with 4-O-6-S-α-Cyanobenzylidene-Protected 6-Thiorhamnopyranosyl Thioglycosides