Access to L- and D-Iminosugar C-Glycosides from a D-gluco-Derived 6-Azidolactol Exploiting a Ring Isomerization/Alkylation Strategy

作者：Mondon Martine; Fontelle Nathalie; Desire Jerome; Lecornue Frederic; Guillard Jerome; Marrot Jerome; Bleriot Yves^*

来源：Organic Letters, 2012, 14(3): 870-873.

DOI：10.1021/ol203385w

A flexible synthetic access to six-membered 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.

• 出版日期2012-2-3