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From Glucose to Cyclooctanic Carbaglucose: A New Class of Carbohydrate Mimetics
Author(s) -
Wang Wei,
Zhang Yongmin,
Sollogoub Matthieu,
Sinaÿ Pierre
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20000717)39:14<2466::aid-anie2466>3.0.co;2-u
Subject(s) - chemistry , regioselectivity , carbohydrate , derivative (finance) , glycoside , hydroboration , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , financial economics , economics
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.