SYNTHESIS OF FUNCTIONALIZED MANNOFURANOSYL GLYCOSIDES - FORMATION OF A MANNO-ANALOG OF SHOWDOMYCIN

Authors
LOPEZHERRERA FJ DOMINGUEZACIEGO RM PINOGONZALEZ MS
Citation
Fj. Lopezherrera et al., SYNTHESIS OF FUNCTIONALIZED MANNOFURANOSYL GLYCOSIDES - FORMATION OF A MANNO-ANALOG OF SHOWDOMYCIN, Anales de quimica, 93(4), 1997, pp. 246-251
Citations number
28
Categorie Soggetti
Chemistry
Journal title
Anales de quimica → ACNP
ISSN journal
11302283
Volume
93
Issue
4
Year of publication
1997
Pages
246 - 251
Database
ISI
SICI code
1130-2283(1997)93:4<246:SOFMG->2.0.ZU;2-D
Abstract
This paper reports the stereoselective synthesis of a manno-analogue o f the antibiotic Showdomycin: 2-(alpha-D-mannofuranosyl)maleimide (7). All intermediates (2, 3, 3, 5 and 6) were confirmed to be alpha-C-gly cosides. The configuration of the glycosidic residue at C-2 was determ ined for 2 by comparing the spectroscopic data of 11, obtained by ster eoselective I-2-induced cyclization from 10.