Practical syntheses of optically active carbagalactose and their potential application to the carbocyclic analogues of KRN7000

Carba-α- and β- 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 1 were accomplished to provide a carba-β- d-galactose derivative 6 in a good yield and with a high stereoselectivity...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2006-11, Vol.17 (21), p.3030-3036
Main Authors: Yu, Seok-Ho, Park, Jeong-Ju, Chung, Sung-Kee
Format: Article
Language:English
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Summary:Carba-α- and β- 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 1 were accomplished to provide a carba-β- 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-α- d-galactose derivative 12 with a high stereoselectivity. An efficient coupling of carba-α-galactose 12 with an aziridine derivative of sphingosine has been demonstrated to give 1- O-carba-α-galactosyl sphingosine derivative 14.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2006.11.014