Synthesis of beta-C-galacto-pyranosides with fluorine on the pseudoanomeric substituent

Org Lett. 2007 Apr 12;9(8):1441-4. doi: 10.1021/ol070169i. Epub 2007 Mar 15.

Abstract

[reaction: see text] beta-C-galacto-Pyranosides with CHF and CF2 substitutes for the glycosidic oxygen were prepared through a four-step sequence starting from a central 1-thio-1,2-O-isopropylidene acetal alcohol and different alpha-fluoro- and alpha,alpha-difluoro acids. The key step in the synthesis is the oxocarbenium cyclization of an intermediate enol ether-thioacetal to a C1-substituted glycal.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Acids / chemistry
  • Fluorine / chemistry*
  • Galactose / chemical synthesis
  • Galactose / chemistry*
  • Glycosides / chemistry
  • Molecular Structure

Substances

  • Acids
  • Glycosides
  • Fluorine
  • Galactose