Synthesis of floridoside

Michel Weïwer, Trevor Sherwood, Robert J. Linhardt

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

Floridoside (2-O-glycerol-α-D-galactopyranoside) is a natural glycerol glycoside found in red algae and is believed to play important roles in carbon storage, transport, and assimilation and in the regulation of osmotic balance. We describe here a rapid, high-yield, and high-stereoselectivity synthesis of floridoside in which the key step involves the 1,2-cis O-glycosylation of 1,3-dibenzylglycerol with ethyl 2,3,4,6-tetra-O-benzyl-1- thio-β-D-galactopyranoside using iodonium dicollidine perchlorate (IDCP) or N-iodosuccinimide/trimethylsilyl triflate (NIS/TMSOTf) as promoters.

Original languageEnglish
Pages (from-to)420-427
Number of pages8
JournalJournal of Carbohydrate Chemistry
Volume27
Issue number7
DOIs
StatePublished - Sep 2008
Externally publishedYes

Keywords

  • 1,2-cis O-glycosylation
  • Floridoside
  • Glycerol glycoside
  • Thioglycoside

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