Synthesis of alpha-fluorosulfonate and alpha-fluorosulfonamide analogues of a sulfated carbohydrate

Org Lett. 2006 Nov 23;8(24):5617-20. doi: 10.1021/ol062357z.

Abstract

The first synthesis of sulfonamide and sulfonate analogues of a sulfated carbohydrate in which the ester oxygen of the sulfate is replaced with a CHF or CF2 group is reported. This was accomplished by electrophilic fluorination of the protected sulfonate and sulfonamide precursors. [reaction: see text].

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bromides / chemistry
  • Carbohydrates / chemical synthesis*
  • Carbohydrates / chemistry
  • Esters / chemistry
  • Fluorides / chemical synthesis*
  • Lithium Compounds / chemistry
  • Magnetic Resonance Spectroscopy
  • Oxygen / chemistry
  • Sulfates / chemistry
  • Sulfuric Acids / chemical synthesis*

Substances

  • Bromides
  • Carbohydrates
  • Esters
  • Lithium Compounds
  • Sulfates
  • Sulfuric Acids
  • lithium bromide
  • fluorosulfonic acid
  • Fluorides
  • Oxygen