From Glucose to Cyclooctanic Carbaglucose: A New Class of Carbohydrate Mimetics

作者：Wei Wang, Yongmin Zhang, Matthieu Sollogoub, Pierre Sînaÿ · 发表于：Angewandte Chemie International Edition · 年份：2000 · DOI：10.1002/1521-3773(20000717)39:14<2466::aid-anie2466>3.0.co;2-u · 被引用次数：63 · 研究领域：Carbohydrate Chemistry and Synthesis、Glycosylation and Glycoproteins Research、Enzyme Catalysis and Immobilization

The sigmatropic rearrangement of the C-vinyl glycoside 2, prepared from methyl α-D-glucoside (1), gives a cyclooctane derivative. Subsequent treatment of the latter by regioselective hydroboration, Tebbe reaction, and debenzylation provides 3—the first member of a new class of carbohydrate mimetics.