Large-scale synthesis of all stereoisomers of a 2,3-unsaturated C-glycoside scaffold

J Org Chem. 2011 Mar 18;76(6):1898-901. doi: 10.1021/jo1022926. Epub 2011 Feb 22.

Abstract

All stereoisomers of a highly functionalized 2,3-unsaturated C-glycoside can be accessed in 10-100 g quantities from readily available starting materials and reagents in 3-7 steps. These chiral scaffolds contain three stereogenic centers along with orthogonally protected functional groups for downstream reactivity.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Glycosides / chemical synthesis*
  • Glycosides / chemistry*
  • Indicators and Reagents / chemistry
  • Stereoisomerism

Substances

  • Glycosides
  • Indicators and Reagents