DE-NOVO SYNTHESIS OF RACEMIC ALTRONOLACTAM AND ARABINONOLACTAM AZASUGARS

Citation
T. Tschamber et al., DE-NOVO SYNTHESIS OF RACEMIC ALTRONOLACTAM AND ARABINONOLACTAM AZASUGARS, Heterocycles, 42(2), 1996, pp. 669-676
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
03855414
Volume
42
Issue
2
Year of publication
1996
Pages
669 - 676
Database
ISI
SICI code
0385-5414(1996)42:2<669:DSORAA>2.0.ZU;2-V
Abstract
Starting from the known peracetylated piperidinose derivatives (7a) an d (7b), the corresponding altrono- and arabinono-lactams (4) and (5) w ere obtained in a straightforward way. A selective two-step hydrolysis of the anomeric acetoxy groups gave the free hydroxyls (8a) and (8b) which were oxidised to the delta-lactams (9a) and (9b), respectively. Deprotection of these latter compounds led to the target molecules.