Catalyst-Controlled, Site-Selective Sulfamoylation of Carbohydrate Derivatives

Org Lett. 2022 Jul 29;24(29):5249-5253. doi: 10.1021/acs.orglett.2c01590. Epub 2022 Jun 21.

Abstract

Methods for site-selective sulfamoylation of secondary hydroxyl groups in pyranosides are described. Using a boronic acid catalyst, selective installation of a Boc-protected sulfamoyl group at the equatorial position of cis-diols in manno- and galacto-configured substrates has been achieved. Activation of trans-diol groups in gluco- and galacto-configured substrates is also possible by employing an organotin catalyst.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols*
  • Boronic Acids*
  • Carbohydrates
  • Catalysis

Substances

  • Alcohols
  • Boronic Acids
  • Carbohydrates