Glycosidation with a disarmed glycosyl iodide: promotion and scope

Org Lett. 2003 Nov 27;5(24):4545-8. doi: 10.1021/ol035475k.

Abstract

[reaction: see text] Glucuronyl iodide 1 has been studied in detail as a "disarmed" glycosyl donor. In a model reaction, using N-iodosuccinimide (NIS) as a promoter and 2-phenylethanol as acceptor, best results were obtained using NIS with I(2), followed by trimethylsilyltrifluoromethanesulfonate (TMSOTf). When a series of primary and secondary alcohols was glycosylated using these conditions, yields of 60-83% of beta-glucuronides were obtained. Various "nonheavy" metal salts also effectively catalyzed the model reaction but led to significant amounts of alpha-product with less reactive secondary alcohols.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry
  • Esters / chemistry
  • Glucuronates / chemistry*
  • Glycosides / metabolism
  • Glycosylation
  • Molecular Structure
  • Phenylethyl Alcohol / chemistry
  • Succinimides / chemistry

Substances

  • Alcohols
  • Esters
  • Glucuronates
  • Glycosides
  • Succinimides
  • methyl 1-deoxy-1-iodo-O(2),O(3),O(4)-triacetylglucuronate
  • N-iodosuccinimide
  • Phenylethyl Alcohol