The synthesis of gracillin and dioscin: two typical representatives of spirostanol glycosides

Carbohydr Res. 2003 Apr 4;338(8):721-7. doi: 10.1016/s0008-6215(03)00004-1.

Abstract

Two representative spirostanol saponins that have the typical structure for the sugar moiety, diosgenyl alpha-L-rhamnopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1-->3)]-beta-D-glucopyranoside (gracillin) and diosgenyl alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->4)]-beta-D-glucopyranoside (dioscin), were easily synthesized by a general approach. A procedure using guanidine for the selective deblocking of acetyl while retaining benzoyl protecting groups is described.

MeSH terms

  • Acetylation
  • Carbohydrate Conformation
  • Diosgenin / analogs & derivatives*
  • Diosgenin / chemical synthesis*
  • Guanidine / chemistry
  • Saponins / chemical synthesis
  • Spirostans / chemical synthesis*

Substances

  • Saponins
  • Spirostans
  • gracillin
  • dioscin
  • Guanidine
  • Diosgenin