De Novo Asymmetric Synthesis of a 6-O-Methyl-d-glycero-l-gluco-heptopyranose-Derived Thioglycoside for the Preparation of Campylobacter jejuni NCTC11168 Capsular Polysaccharide Fragments

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• 作者：Roger A. Ashmus ; Anushka B. Jayasuriya ; Ying-Jie Lim ; George A. O’Doherty ; Todd L. Lowary
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：April 1, 2016
• 年：2016
• 卷：81
• 期：7
• 页码：3058-3063
• 全文大小：403K
• ISSN：1520-6904

文摘

An enantioselective de novo synthesis of a thioglycoside derivative of the 6-O-methyl-d-glycero-l-gluco-heptopyranose residue found in the Campylobacter jejuni NCTC11168 (HS:2) capsular polysaccharide is reported. The compound is obtained from a furfural-derived chiral diol in 11 steps. Notably, compared to the only previous synthesis of this molecule, this approach significantly reduces the number of purification steps required to obtain the target.