STUDIES ON THE SYNTHESIS OF TUNICAMYCIN - THE PREPARATION OF 7-DEOXY-2-DEAMINO-6-HYDROXY TUNICAMINE AND RELATED PRODUCTS

Citation
F. Sarabiagarcia et Fj. Lopezherrera, STUDIES ON THE SYNTHESIS OF TUNICAMYCIN - THE PREPARATION OF 7-DEOXY-2-DEAMINO-6-HYDROXY TUNICAMINE AND RELATED PRODUCTS, Tetrahedron, 52(13), 1996, pp. 4757-4768
Citations number
43
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
00404020
Volume
52
Issue
13
Year of publication
1996
Pages
4757 - 4768
Database
ISI
SICI code
0040-4020(1996)52:13<4757:SOTSOT>2.0.ZU;2-1
Abstract
The condensation of methyl 5-diazo-2,3-O-isopropylidene-beta-D-ribofur anoside with :3,4-di-O-isopropylidene-D-galactohexonodialdo-1,5 pyrano side gave the ketone C-disaccharide 11 as the sole product. This keton e was transformed into different derivatives. Thus, its reduction led stereoselectively to the corresponding alcohols. Similar transformatio ns]ed to the corresponding alkane and amino derivatives, of potential biological interest as inhibitors for glycosidases. These results can be useful for the synthesis of tunicamine and its analogues.