Cyclodextrins selectively modified on both rims using an O-3-debenzylative post-functionalisation, a consequence of the Sorrento meeting

Carbohydr Res. 2012 Jul 15:356:278-81. doi: 10.1016/j.carres.2011.12.002. Epub 2011 Dec 13.

Abstract

A de-O-benzylation reaction induced by I(2)-Et(3)SiH and developed by Iadonisi et al. on mono- and disaccharides was applied to per- or polybenzylated α-cyclodextrins to furnish compounds deprotected at position 3 of all sugar units. This methodology allows the straightforward post-functionalisation of the secondary rim of cyclodextrins already functionalised on their primary rim.

MeSH terms

  • Disaccharides / chemistry*
  • Iodine / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Monosaccharides / chemistry*
  • Silanes / chemistry
  • Stereoisomerism
  • alpha-Cyclodextrins / chemistry*

Substances

  • Disaccharides
  • Monosaccharides
  • Silanes
  • alpha-Cyclodextrins
  • triethylsilane
  • Iodine