SYNTHESIS OF AZASUGARS - UNEXPECTED RESULTS IN THE OXIDATIVE CYCLIZATION OF AMINOALDITOLS

Authors
CIPOLLA L NICOTRA F PANGRAZIO C
Citation
L. Cipolla et al., SYNTHESIS OF AZASUGARS - UNEXPECTED RESULTS IN THE OXIDATIVE CYCLIZATION OF AMINOALDITOLS, Gazzetta chimica italiana, 126(10), 1996, pp. 663-666
Citations number
11
Categorie Soggetti
Chemistry
Journal title
Gazzetta chimica italiana → ACNP
ISSN journal
00165603
Volume
126
Issue
10
Year of publication
1996
Pages
663 - 666
Database
ISI
SICI code
0016-5603(1996)126:10<663:SOA-UR>2.0.ZU;2-R
Abstract
Oxidation with pyridinium chlorochromate of the aminoalditols 3 and 5, obtained by reaction of a protected aldose with a primary amine and t hen with a Grignard reagent, affords alpha-keto-acid derivatives which undergo decarboxylation to lactams 4 and 6. Starting from 2,3,5-tri-O -benzyl-D-arabinose, lactam 4 is the only product, whereas starting fr om 2,3,4,6-tetra-O-benzyl-D-glucose or -mannose, alpha-keto ester 7 is the main product.