C(4)-C(5) pyranoid ring opening in 2-C : 1-N-carbonyl-2-deoxy-alpha-D-glucopyranosylamine

Authors
Belzecki, C Chmielewski, M
Citation
C. Belzecki et M. Chmielewski, C(4)-C(5) pyranoid ring opening in 2-C : 1-N-carbonyl-2-deoxy-alpha-D-glucopyranosylamine, POL J CHEM, 74(9), 2000, pp. 1243-1248
Citations number
12
Categorie Soggetti
Chemistry
Journal title
POLISH JOURNAL OF CHEMISTRY
ISSN journal
01375083 → ACNP
Volume
74
Issue
9
Year of publication
2000
Pages
1243 - 1248
Database
ISI
SICI code
0137-5083(200009)74:9<1243:CPROI2>2.0.ZU;2-T
Abstract
2-C: 1 -N-Carbonyl-2-deoxy-3,4,6-tris-O-trimethylsilyl-alpha-D-glucopyranos ylamine 1 was subjected to the reaction sequence leading to the introductio n of the C(4)-C(5) double bond into the pyranoid ring. Ozonolysis of the C( 4)-C(5) double bond in the sugar 14 cleaved the six-membered ring to afford 4-acyloxy azetidinone 15 suitable for further carbapenem and carbacephem s yntheses.