RADICAL-MEDIATED SYNTHESIS OF N-ACETYL-D-GALACTOSAMINE CONTAINING C-DISACCHARIDES VIA A TEMPORARY PHOSPHORAMIDIC CONNECTION

Authors
RUBINSTENN G ESNAULT J MALLET JM SINAY P
Citation
G. Rubinstenn et al., RADICAL-MEDIATED SYNTHESIS OF N-ACETYL-D-GALACTOSAMINE CONTAINING C-DISACCHARIDES VIA A TEMPORARY PHOSPHORAMIDIC CONNECTION, Tetrahedron : asymmetry, 8(8), 1997, pp. 1327-1336
Citations number
46
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
8
Year of publication
1997
Pages
1327 - 1336
Database
ISI
SICI code
0957-4166(1997)8:8<1327:RSONCC>2.0.ZU;2-1
Abstract
The C-disaccharide {alpha-D-GalNAc-C-(1-->4)-beta-D-Glc-OMe} and its i nterglycosidic beta anomer were synthesized by radical coupling of phe nyl -benzyl-2-deoxy-1-seleno-alpha-D-galactopyranoside onto methyl -4- deoxy-4-C-methylene-beta-D-xylo-hexopyranoside, which are temporarily connected through a phosphoramido tether. A similar reaction was perfo rmed with methyl -4-deoxy-4-C-methylene-alpha-D-xylo-hexopyranoside to produce the two closely related alpha-OMe C-disaccharides. (C) 1997 E lsevier Science Ltd.