Tuning effect of silyl protecting groups on the glycosylation reactivity of arabinofuranosyl thioglycosides

Org Lett. 2013 Jun 7;15(11):2834-7. doi: 10.1021/ol401166x. Epub 2013 May 17.

Abstract

The tuning effect of silyl protecting groups on the glycosylation reactivity of arabinofuranosyl phenyl thioglycoside donors is presented. Silyl ethers on the 3-, 5-, and 3,5-positions of the arabinofuranose ring are found to have an arming effect on the donor reactivity, whereas the cyclic 3,5-acetal type protecting groups reduce the reactivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Arabinose / analogs & derivatives*
  • Arabinose / chemistry
  • Glycosylation
  • Molecular Structure
  • Stereoisomerism
  • Thioglycosides / chemistry*
  • Trimethylsilyl Compounds / chemistry*

Substances

  • Thioglycosides
  • Trimethylsilyl Compounds
  • arabinofuranose
  • Arabinose