Synthesis of Rare Carbohydrates and Analogues Starting from Enantiomerically Pure 7-Oxabicyclo[2.2.1]heptyl Derivatives (“NakedSugars”)

Title: Synthesis of Rare Carbohydrates and Analogues Starting from Enantiomerically Pure 7-Oxabicyclo[2.2.1]heptyl Derivatives (“NakedSugars”)

Volume: 4 Issue: 5

Author(s): Pierre Vogel

Affiliation:

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.

Cite this article as:

Vogel Pierre, Synthesis of Rare Carbohydrates and Analogues Starting from Enantiomerically Pure 7-Oxabicyclo[2.2.1]heptyl Derivatives (“NakedSugars”), Current Organic Chemistry 2000; 4 (5) . https://dx.doi.org/10.2174/1385272003376175