The first hetero-bifunctionalization of the secondary face of beta-cyclodextrin: selective and efficient conversion of the A-ring of a 2A,2B-disulfonate to 2A,3A-epoxymannoside

Chem Commun (Camb). 2005 Jul 7:(25):3168-70. doi: 10.1039/b502573g. Epub 2005 May 18.

Abstract

The A-ring of 2(A),2(B)-O,O-di(mesitylenesulfonyl)-beta-cyclodextrin was converted to 2(A),3(A)-epoxymannoside without affecting the other sulfonylated residue, which affords the first approach to hetero-bifunctionalization at the secondary hydroxyl side of cyclodextrins.

MeSH terms

  • Mannosides / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Sulfonic Acids / chemistry*
  • beta-Cyclodextrins / chemistry*

Substances

  • Mannosides
  • Sulfonic Acids
  • beta-Cyclodextrins
  • betadex