Divergent syntheses of all 16 carbasugar stereoisomers via stereoconversion of carba-β- d-altropyranose derivatives

We have developed practical synthetic routes to enantiopure d- and l-carba-β-altrose derivatives and all the possible stereoisomers via their divergent stereoconversions. Carba-β- d-altrose was prepared from 3-cyclohexene-1-carboxylic acid and converted to carba-β- d-mannose, carba-β- d-idose, and c...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2005-08, Vol.16 (16), p.2729-2747
Main Authors: Yu, Seok-Ho, Chung, Sung-Kee
Format: Article
Language:English
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Summary:We have developed practical synthetic routes to enantiopure d- and l-carba-β-altrose derivatives and all the possible stereoisomers via their divergent stereoconversions. Carba-β- d-altrose was prepared from 3-cyclohexene-1-carboxylic acid and converted to carba-β- d-mannose, carba-β- d-idose, and carba-β- d-talose derivatives via regio- and stereoselective oxidation/reduction of 3-OH and/or 4-OH. The four carbasugar stereoisomers were then transformed to the remaining 12 carbasugar stereoisomers and their 1,2-epoxides by regio- and stereoselective manipulation of hydroxyl groups in C1 and C2, which includes oxidation/reduction, Mitsunobu’s reaction, olefination/dihydroxylation, and epoxidation/ring-opening protocols.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2005.07.010