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

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• 作者：Abhijit Sau^a ; Rajib Panchadhayee^a ; Debjani Ghosh^b ; Anup Kumar Misra^a ; ^{akmisra69@gmail.com}
• 关键词：Salmonella enterica ; Glycosylation ; O-Polysaccharide ; Stereoselectivity ; Tetrasaccharide
• 刊名：Carbohydrate Research
• 出版年：2012
• 出版时间：1 May, 2012
• 年：2012
• 卷：352
• 期：Complete
• 页码：18-22
• 全文大小：462 K

文摘

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.