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 language | English |
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Pages (from-to) | 18-22 |
Number of pages | 5 |
Journal | Carbohydrate Research |
Volume | 352 |
DOIs | |
Publication status | Published - 1 May 2012 |
Keywords
- Glycosylation
- O-Polysaccharide
- Salmonella enterica
- Stereoselectivity
- Tetrasaccharide