SYNTHESIS AND CONFORMATIONAL PROPERTIES OF SUGAR AMIDES AND THIOAMIDES

Authors
MELLET CO MARIN AM FERNANDEZ JMG FUENTES J
Citation
Co. Mellet et al., SYNTHESIS AND CONFORMATIONAL PROPERTIES OF SUGAR AMIDES AND THIOAMIDES, Tetrahedron : asymmetry, 5(12), 1994, pp. 2313-2324
Citations number
35
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
5
Issue
12
Year of publication
1994
Pages
2313 - 2324
Database
ISI
SICI code
0957-4166(1994)5:12<2313:SACPOS>2.0.ZU;2-D
Abstract
The synthesis of deoxythioformamido and deoxythioacetamido derivatives of 2:3,4-di-O-isopropylidene-alpha-D-galactopyranose, 1,2:3,5-di-O-is opropylidene-alpha-D-glucofuranose and 2,3:4,5-di-O-isopropylidene-bet a-D-fructopyranose at the primary carbon atom has been effected by thi onation of the corresponding sugar amides. Formamides and thioformamid es existed as a mixture of the Z (major) and E (minor) stereomers arou nd the N-C(=X) bond in CDCl3 solutions, while the Z rotamer was the so le one detected in the cases of acetamides and thioacetamides.