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Org Lett. 2004 Oct 14;6(21):3797-800.

Stereospecific synthesis of 1,2-cis glycosides by vinyl-mediated IAD.

Author information

1
The Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK.

Abstract

[reaction: see text] Stereospecific 1,2-cis glycosylation of 2-O-vinyl thioglycosides, synthesized from the corresponding alcohols by Ir-catalyzed transvinylation with vinyl acetate, is achieved by iodine-mediated tethering of a range of primary and secondary carbohydrate acceptors, followed by intramolecular aglycon delivery (IAD). The use of such an intramolecular glycosylation strategy furnishes the desired alpha-gluco and beta-manno disaccharides in an entirely stereoselective manner.

PMID:
15469352
DOI:
10.1021/ol048427o

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