Access to l- and d-Iminosugar C-Glycosides from a d-gluco-Derived 6-Azidolactol Exploiting a Ring Is

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• 作者：Martine Mondon ; Nathalie Fontelle ; J茅r么me D茅sir茅 ; Fr茅d茅ric Lecornu茅 ; J茅r么me Guillard ; J茅r么me Marrot ; Yves Bl茅riot
• 刊名：Organic Letters
• 出版年：2012
• 出版时间：February 3, 2012
• 年：2012
• 卷：14
• 期：3
• 页码：870-873
• 全文大小：264K
• 年卷期：v.14,no.3(February 3, 2012)
• ISSN：1523-7052

文摘

A flexible synthetic access to six-membered l- and d-iminosugar C-glycosides is reported starting from the easily available 6-azido-6-deoxy-2,3,4-tri-O-benzyl-d-glucopyranose precursor. This methodology involves a highly diastereoselective tandem ring enlargement/alkylation and a stereocontrolled ring contraction. It allows an efficient synthesis of iminosugar C-glycosides displaying structural diversity at both C-1 and C-6.