Concise synthesis of C-1-cyano-iminosugars via a new Staudinger/aza Wittig/Strecker multicomponent reaction strategy

Bioorg Med Chem Lett. 2014 Jun 15;24(12):2777-80. doi: 10.1016/j.bmcl.2014.03.069. Epub 2014 Apr 1.

Abstract

A new Staudinger/aza Wittig/Strecker multicomponent reaction sequence to C-1-cyano iminoalditols has been developed. When applied to 5-azidodeoxy-d-xylose and -d-glucose as substrates the method leads smoothly in good yield and with excellent stereoselectivity to respectively, 1,5-dideoxy-1,5-imino-d-idurono nitrile and 2,6-didesoxy-2,6-imino-d-glycero-d-ido-heptononitrile.

Keywords: C-1-cyano-iminosugar building blocks; Glucocerebrosidase; Glycosidase inhibitor; Iminoalditol; Staudinger/aza Wittig Strecker multicomponent reaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aza Compounds / chemistry
  • Crystallography, X-Ray
  • Imino Pyranoses / chemical synthesis*
  • Imino Pyranoses / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Nitriles / chemistry*
  • Stereoisomerism

Substances

  • Aza Compounds
  • Imino Pyranoses
  • Nitriles