Synthesis of a tetrasaccharide analog corresponding to the repeating unit of the O-polysaccharide of Salmonella enterica O59: Unexpected stereo outcome in glycosylation

Abhijit Sau, Rajib Panchadhayee, Debjani Ghosh, Anup Kumar Misra*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

10 Citations (Scopus)

Abstract

Convergent synthesis of a tetrasaccharide analog corresponding to the repeating unit of the O-polysaccharide of Salmonella enterica O59 is presented. A thioglycoside disaccharide donor was prepared by the glycosylation of two thioglycosides by tuning their relative reactivity. An unexpected stereochemical outcome was observed in a glycosylation using an ethyl 2-O-acetyl-3-O-benzyl-4, 6-O-bensylidene-thio-galactoside donor, where the alpha-galactoside was formed in spite of the presence of the 2-O-acetyl participating group.

Original languageEnglish
Pages (from-to)18-22
Number of pages5
JournalCarbohydrate Research
Volume352
DOIs
Publication statusPublished - 1 May 2012

Keywords

  • Glycosylation
  • O-Polysaccharide
  • Salmonella enterica
  • Stereoselectivity
  • Tetrasaccharide

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