Synthesis of Hexenuloses and a Library of Disaccharides Possessing 3-oxo-glycal Unit

J Org Chem. 2022 Jul 15;87(14):8939-8955. doi: 10.1021/acs.joc.2c00663. Epub 2022 Jun 30.

Abstract

An expeditious method for the synthesis of monosaccharides and disaccharides possessing 3-oxo-glycal units is revealed. Several monosaccharides and disaccharide-derived glycals are converted to the corresponding hexenuloses in three steps involving halo-alkoxylation, dehydrohalogenation, and ketalyzation reactions. A number of 3-oxo-glycals are synthesized to show the methodology's importance and generality. Further, the protocol is successfully applied to synthesize a rare-sugar disaccharide donor unit present as part of the trisaccharide moiety in the reported natural product, versipelostatin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Disaccharides*
  • Monosaccharides*
  • Trisaccharides

Substances

  • Disaccharides
  • Monosaccharides
  • Trisaccharides