Synthesis of the laminara-oligosaccharide methyl beta-glycosides of dp 3-8

Carbohydr Res. 1993 Jul 5;245(1):81-96. doi: 10.1016/0008-6215(93)80061-i.

Abstract

Ethyl 2,3,4,6-tetra-O-acetyl-1-thio-alpha-D-glucopyranoside has been prepared in a good yield by anomerization of the corresponding beta-thioglucoside with tin(IV) chloride and transformed, in three steps, into ethyl 2-O-benzoyl-4,6-O-benzylidene-1-thio-alpha-D-glucopyranoside (18). Chloroacetylation of 18, followed by treatment of the product with chlorine gave crystalline 2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-beta-D-glucopyranosyl chloride (20). This was coupled with methanol in the presence of silver carbonate-silver perchlorate and the product was O-dechloroacetylated to afford methyl 2-O-benzoyl-4,6-O-benzylidene-beta-D-glucopyranoside (22). Silver triflate-promoted glucosylation of 18 with 20 gave a beta-(1-->3)-linked disaccharide derivative, reaction of which with chlorine yielded crystalline O-(2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-beta-D-glucopyranosyl) - (1-->3)-2-O-benzoyl-4,6-O-benzylidene-beta-D-glucopyranosyl chloride (24). Likewise, condensation of 22 with 20 gave a beta-(1-->3)-linked disaccharide glycoside, which was partially deprotected to give methyl O-(2-O-benzoyl-4,6-O-benzylidene-beta-D-glucopyranosyl)-(1-->3)-2-O-benz oyl- 4,6-O-benzylidene-beta-D-glucopyranoside (26). The methyl beta-glycosides of a homologous series of (1-->3)-linked beta-D-gluco-oligosaccharides from the tri- to the octa-saccharide have been synthesized in a blockwise manner by using 22 and 26 as the glycosyl acceptors, 24 as the disaccharide donor, and silver triflate as the promoter.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Methylglycosides*
  • Molecular Sequence Data
  • Oligosaccharides / chemical synthesis*
  • Oligosaccharides / chemistry
  • Optical Rotation

Substances

  • Indicators and Reagents
  • Methylglycosides
  • Oligosaccharides