A synthesis of carbasugar-sugar pseudodisaccharides via a cycloaddition-cycloreversion reaction of 2H-pyran-2-ones

Org Lett. 2010 Dec 3;12(23):5564-6. doi: 10.1021/ol102358s. Epub 2010 Nov 8.

Abstract

Cycloaddition of 3-carbomethoxy-2H-pyran-2-one to a vinylated sugar followed by the loss of bridging CO(2) from the cycloadduct affords a cyclohexadiene which can be manipulated to a carbasugar-sugar pseudodisaccharide.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbasugars / chemistry*
  • Cyclization
  • Disaccharides / chemical synthesis*
  • Hydrogen / chemistry*
  • Molecular Structure
  • Pyrans / chemistry*

Substances

  • Carbasugars
  • Disaccharides
  • Pyrans
  • Hydrogen