Synthesis of nitrogen-functionalized beta-cycloaltrins

J Org Chem. 2004 Dec 10;69(25):8942-5. doi: 10.1021/jo0488457.

Abstract

We report the synthesis of functionalized beta-cycloaltrins having azido groups at C-3, C-6, and both C-3 and C-6 by nucleophilic epoxy ring-opening of per-2,3-anhidro-beta-cyclomannin derivatives. The value of these compounds as templates for further functionalization is exemplified by the conversion of heptakis(3,6-diazido-3,6-dideoxy)-beta-cycloaltrin into the per-3,6-diamino, per-3,6-diacetamido, per-3,6-dichloroacetamido, and per[3,6-bis(N'-ethylureido)] derivatives in good yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Epoxy Compounds / chemical synthesis
  • Epoxy Compounds / chemistry
  • Nitrogen / chemistry*
  • Stereoisomerism
  • beta-Cyclodextrins / chemical synthesis*
  • beta-Cyclodextrins / chemistry*

Substances

  • Epoxy Compounds
  • beta-Cyclodextrins
  • Nitrogen