Effective synthesis of 1beta-acyl glucuronides by selective acylation

Org Lett. 2005 Jun 23;7(13):2591-4. doi: 10.1021/ol0507165.

Abstract

[reaction: see text] Acyl glucuronides are vital metabolites for many carboxylic acid containing drugs. We report an efficient new method for the chemical synthesis of these molecules by selective 1beta-acylation of allyl glucuronate with carboxylic acids catalyzed by HATU and then mild deprotection through treatment with Pd(PPh(3))(4) and morpholine. The method is effective for a range of aryl and alkyl carboxylic acids, including important drugs.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acylation
  • Carboxylic Acids / chemistry*
  • Glucuronides / chemical synthesis*
  • Glucuronides / chemistry
  • Molecular Structure
  • Morpholines / chemistry
  • Organometallic Compounds / chemistry
  • Palladium / chemistry
  • Stereoisomerism

Substances

  • Carboxylic Acids
  • Glucuronides
  • Morpholines
  • Organometallic Compounds
  • Palladium