Stereoselective Synthesis of D-5-Homo-4-selenoribose as a Versatile Intermediate for 4'-Selenonucleosides

Org Lett. 2015 Sep 18;17(18):4636-9. doi: 10.1021/acs.orglett.5b02393. Epub 2015 Sep 8.

Abstract

Stereoselective synthesis of D-5-homo-4-selenoribose, serving as a versatile intermediate for the synthesis of 4'-selenonucleosides 12a-c, was accomplished using Sharpless asymmetric epoxidation, regioselective cleavage of the α,β-epoxide, and stereoselective reduction of the ketone as the key steps.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Epoxy Compounds / chemistry
  • Molecular Structure
  • Nucleosides / chemical synthesis*
  • Nucleosides / chemistry
  • Organoselenium Compounds / chemical synthesis*
  • Organoselenium Compounds / chemistry
  • Stereoisomerism

Substances

  • D-5-homo-4-selenoribose
  • Epoxy Compounds
  • Nucleosides
  • Organoselenium Compounds