Practical syntheses of optically active carbagalactose and their potential application to the carbocyclic analogues of KRN7000
SCIE
SCOPUS
- Title
- Practical syntheses of optically active carbagalactose and their potential application to the carbocyclic analogues of KRN7000
- Authors
- Yu, SH; Park, JJ; Chung, SK
- Date Issued
- 2006-11-17
- Publisher
- PERGAMON-ELSEVIER SCIENCE LTD
- Abstract
- Carba-alpha- and beta-D-galactose derivatives were efficiently prepared from a cyclohex-3-ene-1,2-diol derivative 1. Regioselective inversion of 2-OH, and stereoselective dihydroxylation of I were accomplished to provide a carba-p-D-galactose derivative 6 in a good yield and with a high stereoselectivity. Stereo-inversion of 1-OH of 6 via oxidation/reduction gave carba-beta-D-galactose derivative 12 with a high stereoselectivity. An efficient coupling of carba-alpha-galactose 12 with an aziridine derivative of sphingosine has been demonstrated to give 1-O-carba-alpha-galactosyl sphingosine derivative 14. (c) 2006 Elsevier Ltd. All rights reserved.
- Keywords
- KILLER T-CELLS; ALPHA-GALACTOSYLCERAMIDES; STEREOSELECTIVE-SYNTHESIS; CARBA-SUGARS; CARBASUGARS; DERIVATIVES; PSEUDOSUGARS; OLIGOSACCHARIDES; SPHINGOSINE; CHEMISTRY
- URI
- https://oasis.postech.ac.kr/handle/2014.oak/23625
- DOI
- 10.1016/j.tetasy.2006.11.014
- ISSN
- 0957-4166
- Article Type
- Article
- Citation
- TETRAHEDRON-ASYMMETRY, vol. 17, no. 21, page. 3030 - 3036, 2006-11-17
- Files in This Item:
- There are no files associated with this item.
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.