Synthesis of Rare Carbohydrates and Analogues Starting from Enantiomerically Pure 7-Oxabicyclo(2.2.1)heptyl Derivatives (Naked Sugars)

Author: Vogel P.

Source: Current Organic Chemistry, Volume 4, Number 5, May 2000 , pp. 455-480(26)

Publisher: Bentham Science Publishers

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Abstract:

Recent applications of the naked sugar methodology are reviewed. General methods have been developed to transform enantiomerically pure 7-oxabicyclo?(2.2.1)heptyl derivatives into rare monosaccharides, carbasugars, into a new doubly-branched imino-dideoxyalditol (iminosugar), into long-chain carbohydrates, C-disaccharides, imino-C-disaccharides and new polyhydroxylated quinolizidines. The methods allow to prepare both enantiomers of a given target with the same ease. Predictable high stereoselectivity of the reactions of the bicyclic chirons adds to the flexibility of the approach that can lead to a large molecular diversity.

Keywords: Rare carbohydrates; Imino dideoxyalditol; Carbohydrates; C disaccharides; Imino C disaccharides; Bicyclic chirons; Naked sugars; Diels Alder additions; Regioselective carbon; Carbon bond formation; Palladium; Carbonylative stille coupling; Mitsunobu displacement reaction; Carbapyranoses and analogues; Inhibitors of beta galactosidase; Doubly branched imino sugar; Long chain carbohydrates; Phosphodiesterase inhibitors; Xanthomonas oryzae; C Disaccharides; Indolizidine alkaloids; Castanospermine; Glycosidase inhibitors