Use of phenyl 2-alpha-selenoglycosides of N-acetylneuraminic acid as a glycosyl donor for the glycosylation reactions

Bioorg Med Chem Lett. 2002 Sep 2;12(17):2309-11. doi: 10.1016/s0960-894x(02)00400-6.

Abstract

Phenyl 2-alpha-selenoglycosides of Neu5Ac were successfully prepared from the corresponding peracetylated chloro derivative of Neu5Ac 1 and phenylselenol in the presence of N,N-di-isopropylethylamine in excellent yields. The reaction of with various alcohols was effectively catalyzed by NIS/TfOH or DMTST to produce a variety of glycosides in moderate yields. Selective activation of over phenyl 2-alpha-thioglycoside of Neu5Ac with AgOTf/K(2)CO(3) was also achieved.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Glycosides / chemical synthesis
  • Glycosylation
  • N-Acetylneuraminic Acid / analogs & derivatives*
  • Selenium Compounds / chemistry*
  • Stereoisomerism

Substances

  • Glycosides
  • Selenium Compounds
  • N-Acetylneuraminic Acid