Recent advances in stereoselective glycosylation through intramolecular aglycon delivery

Org Biomol Chem. 2010 Aug 21;8(16):3596-608. doi: 10.1039/c004281a. Epub 2010 Jun 28.

Abstract

Methodology toward the stereoselective 1,2-cis glycoside linkage using intramolecular aglycon delivery (IAD) has been extensively developed. In the last two decades, progress has been made using various mixed acetal linkages and a number of glycosyl donor moieties to develop novel IAD strategies, mainly based on formation of acetal linkages. This account summarizes the newest naphthylmethyl (NAP) ether-mediated IAD as well as all the types of mediations for stereospecific construction of various 1,2-cis linkages, not only for beta-mannopyranoside, but also for other linkages almost without exception, including beta-L-rhamnoside.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetals / chemistry
  • Glycosides / chemistry*
  • Glycosylation
  • Ketones / chemistry
  • Molecular Structure
  • Stereoisomerism

Substances

  • Acetals
  • Glycosides
  • Ketones