Hypervalent iodine mediated synthesis of C-2 deoxy glycosides and amino acid glycoconjugates

J Org Chem. 2014 May 16;79(10):4470-6. doi: 10.1021/jo500465m. Epub 2014 May 5.

Abstract

A simple, efficient, and practical method for the synthesis of C-2 deoxy-2-iodo glycoconjugates in self-assembled structures was found using PhI(OCOR)2. 2-Iodo glycoserinyl esters were intramolecularly converted into 2-iodo serinyl glycosides which upon dehalogenation gave C-2 deoxy amino acid glycoconjugates.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Glycoconjugates / chemical synthesis*
  • Glycoconjugates / chemistry
  • Glycosides / chemical synthesis*
  • Glycosides / chemistry
  • Iodine / chemistry*
  • Magnetic Resonance Spectroscopy
  • Rhodium / chemistry*
  • Stereoisomerism

Substances

  • Amino Acids
  • Glycoconjugates
  • Glycosides
  • Iodine
  • Rhodium