Synthesis of the trisaccharide portion of soyasaponin beta g: evaluation of a new glucuronic acid acceptor

Carbohydr Res. 2003 Jul 4;338(14):1441-54. doi: 10.1016/s0008-6215(03)00195-2.

Abstract

The synthesis of the trisaccharide portion of soyasaponin beta g was successfully achieved using a new glucuronic acid acceptor: methyl 1-O-allyl-3,4-di-O-methoxymethyl-beta-D-glucuronate (9). This compound and methyl 1-O-allyl-3,4-di-O-tert-butyldimethylsilyl-beta-D-glucuronate (8) were both prepared from glucuronolactone via a glycal intermediate. The former compound 9 was successfully coupled to ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-beta-D-galactopyranoside (13) in excellent yield. Synthesis of the protected trisaccharide was then completed by the addition of a suitably protected rhamnose derivative to the disaccharide portion. The reactivity of the glucuronic acid derivative 9 was also explored with trichloroacetimidate and fluoride donors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Sequence
  • Glucuronates / chemistry*
  • Models, Chemical
  • Molecular Sequence Data
  • Molecular Structure
  • Oleanolic Acid / analogs & derivatives*
  • Oleanolic Acid / chemistry*
  • Saponins / chemistry*
  • Trisaccharides / chemical synthesis*

Substances

  • Glucuronates
  • Saponins
  • Trisaccharides
  • soyasaponin beta g
  • Oleanolic Acid