Is donor-acceptor hydrogen bonding necessary for 4,6-O-benzylidene-directed beta-mannopyranosylation? Stereoselective synthesis of beta-C-mannopyranosides and alpha-C-glucopyranosides.

Abstract

2,3-Di-O-benzyl-4,6-O-benzylidene-thiohexopyranosides, on activation with 1-benzenesulfinyl piperidine and triflic anhydride, react with allyl silanes and stannanes, and with silyl enolethers to give C-glycosides. In the mannose series the beta-isomers are formed selectively whereas the glucose series provides the alpha-anomers. This selectivity pattern parallels that of O-glycoside formation and eliminates the need to consider donor-acceptor hydrogen bonding in the formation of the O-glycosides.

DOI: 10.1021/ol8017038

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Cite this paper

@article{Crich2008IsDH, title={Is donor-acceptor hydrogen bonding necessary for 4,6-O-benzylidene-directed beta-mannopyranosylation? Stereoselective synthesis of beta-C-mannopyranosides and alpha-C-glucopyranosides.}, author={David Crich and Indrajeet Sharma}, journal={Organic letters}, year={2008}, volume={10 21}, pages={4731-4} }