SYNTHESIS OF 2,6-DIDEOXY-4-S-METHYL-4-THIO-D-RIBO-HEXOPYRANOSE, A COMPONENT OF THE ESPERAMICIN OLIGOSACCHARIDE

Authors
DUPRADEAU FY PRANDI J BEAU JM
Citation
Fy. Dupradeau et al., SYNTHESIS OF 2,6-DIDEOXY-4-S-METHYL-4-THIO-D-RIBO-HEXOPYRANOSE, A COMPONENT OF THE ESPERAMICIN OLIGOSACCHARIDE, Tetrahedron, 51(11), 1995, pp. 3205-3220
Citations number
61
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
11
Year of publication
1995
Pages
3205 - 3220
Database
ISI
SICI code
0040-4020(1995)51:11<3205:SO2AC>2.0.ZU;2-R
Abstract
Two synthetic approaches to 2,6-dideoxy-4-S-methyl-4-thio-D-ribo pyran ose, a component of the oligosaccharide of esperamicins are described. An asymmetric synthesis, starting from the propargylic alcohol dimer, relies on the Sharpless asymmetric epoxidation and the regioselective opening of epoxy alcohols. The other synthesis is based on stereocont rolled transformations of a readily available sugar precursor, D-galac tose.