Synthesis of a Pseudodisaccharide Suitable for Synthesis of Ring I Modified 4,5-2-Deoxystreptamine Type Aminoglycoside Antibiotics

J Org Chem. 2020 Jun 5;85(11):7583-7587. doi: 10.1021/acs.joc.0c00743. Epub 2020 May 8.

Abstract

To facilitate the synthesis of paromomycin and/or neomycin analogues, we describe a cleavage of ring I from paromomycin that proceeds in the presence of azides and affords a glycosyl acceptor for the installation of a modified ring I. A paromomycin 4',6'-diol is oxidized by the Dess-Martin periodinane followed by m-chloroperoxybenzoic acid. Base treatment then affords a protected pseudodisaccharide, which functions as a glycosyl acceptor. The method should also apply to the cleavage of pyranosyl 4,6-diols from oligosaccharides and glycoconjugates.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Aminoglycosides*
  • Anti-Bacterial Agents*
  • Hexosamines
  • Neomycin
  • Paromomycin

Substances

  • Aminoglycosides
  • Anti-Bacterial Agents
  • Hexosamines
  • Paromomycin
  • Neomycin
  • 2-deoxystreptamine