Synthesis of saponins using partially protected glycosyl donors

Org Lett. 2003 Oct 2;5(20):3627-30. doi: 10.1021/ol035353s.

Abstract

[reaction: see text] A new class of glycosyl donors having unprotected 2- and 2,4-hydroxyl groups were investigated under the standard glycosylation conditions. This approach was shown to be generally effective for the synthesis of alkyl and steroidal glycosides. A natural saponin, containing 2,4-branched oligosaccharide, was prepared in 35% overall yield in four straightforward sequential reactions by taking advantage of these partially protected donors.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Glycosylation
  • Oligosaccharides / chemical synthesis
  • Saponins / chemical synthesis*
  • Stereoisomerism

Substances

  • Oligosaccharides
  • Saponins