Preparation of sucrose heptaesters unsubstituted at the C-1 hydroxy group of the fructose moiety via selective O-desilylation

Carbohydr Res. 2000 Sep 22;328(3):419-23. doi: 10.1016/s0008-6215(00)00119-1.

Abstract

Selective O-desilylation of 6,1',6'-tri-O-tert-butyldiphenylsilyl-2,3,4,3',4'-penta-O-benzo ylsucrose with hydrofluoric acid in acetonitrile led to the 1'-O-tert-butyldiphenylsilyl derivative (96% yield), which was further perbenzoylated and deprotected at OH-1' with tetrabutylammonium fluoride (86%). An analogous sequence with the corresponding O-acetylated sucrose derivative and tetrabutylammonium fluoride as desilylating agent resulted in a lower yield of the C-1' hydroxy derivative.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Esters / chemical synthesis*
  • Esters / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Sucrose / analogs & derivatives*
  • Sucrose / chemistry*

Substances

  • Esters
  • Sucrose