Synthesis of glycosyl phosphates from 1,2-orthoesters and application to in situ glycosylation reactions

Org Lett. 2006 Apr 27;8(9):1815-8. doi: 10.1021/ol0603155.

Abstract

[reaction: see text] A series of glycosyl phosphates were prepared in high yield by treatment of the corresponding 1,2-orthoesters with dibutyl phosphate. Glycosyl phosphates are efficient glycosylating agents even when used in crude form or when generated in situ. The immunodominant epitope trirhamnoside of group B Streptococcus was prepared to demonstrate the synthetic utility of the method.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Epitopes / drug effects*
  • Epitopes / genetics
  • Glycosides / chemistry*
  • Glycosylation
  • Molecular Structure
  • Streptococcus / drug effects*
  • Streptococcus / genetics
  • Sugar Phosphates / chemical synthesis*

Substances

  • Epitopes
  • Glycosides
  • Sugar Phosphates