A highly concise preparation of O-deacetylated arylthioglycosides of N-acetyl-D-glucosamine from 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-alpha-D-glucopyranosyl chloride and aryl thiols or disulfides

Carbohydr Res. 2006 Jul 24;341(10):1764-9. doi: 10.1016/j.carres.2005.12.009. Epub 2006 Feb 10.

Abstract

An expedient and mild route to a range of aryl 2-acetamido-2-deoxy-1-thio-beta-D-glucopyranosides has been devised from 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-alpha-D-glucopyranosyl chloride and arylthiols or aryl disulfides using phase transfer catalysis conditions. This simple procedure compresses up to three synthetic steps into a one-pot reaction, obviating the need for tedious workups and chromatography and directly furnishes crystalline materials in good yields. The procedure is compatible with a range of thiols and disulfides and may be amenable for preparing a wide range of thioglycosides with various glycons and aglycons.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylglucosamine / analogs & derivatives
  • Acetylglucosamine / chemistry*
  • Disulfides / chemistry*
  • Sulfhydryl Compounds / chemistry*
  • Thioglycosides / chemical synthesis*

Substances

  • Disulfides
  • Sulfhydryl Compounds
  • Thioglycosides
  • Acetylglucosamine