Divergent syntheses of all 16 carbasugar stereoisomers via stereoconversion of carba-beta-D-altropyranose derivatives
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- Title
- Divergent syntheses of all 16 carbasugar stereoisomers via stereoconversion of carba-beta-D-altropyranose derivatives
- Authors
- Yu, SH; Chung, SK
- Date Issued
- 2005-08-22
- Publisher
- PERGAMON-ELSEVIER SCIENCE LTD
- Abstract
- We have developed practical synthetic routes to enantiopure D- and L-carba-beta-altrose derivatives and all the possible stereoisomers via their divergent stereoconversions. Carba-beta-D-altrose was prepared from 3-cyclohexene-l-carboxylic acid and converted to carba-beta-D-mannose, carba-beta-D-idose, and carba-beta-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. (c) 2005 Elsevier Ltd. All rights reserved.
- Keywords
- SIALYLTRANSFERASE INHIBITORS; STEREOSELECTIVE-SYNTHESIS; INOSITOL STEREOISOMERS; CARBOCYCLIC ANALOGS; VICINAL DIOLS; PSEUDOSUGARS; SUGARS; IMINO; EPOXIDES; ETHER
- URI
- https://oasis.postech.ac.kr/handle/2014.oak/24407
- DOI
- 10.1016/j.tetasy.2005.07.010
- ISSN
- 0957-4166
- Article Type
- Article
- Citation
- TETRAHEDRON-ASYMMETRY, vol. 16, no. 16, page. 2729 - 2747, 2005-08-22
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