Application of 2,3-aziridino-gamma-lactone methodology toward the enantiospecific synthesis of the (3S,4S)-isomer of dihydroxy-L-glutamic acid

Authors
Dauban, P de Saint-Fuscien, C Dodd, RH
Citation
P. Dauban et al., Application of 2,3-aziridino-gamma-lactone methodology toward the enantiospecific synthesis of the (3S,4S)-isomer of dihydroxy-L-glutamic acid, TETRAHEDRON, 55(24), 1999, pp. 7589-7600
Citations number
47
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
24
Year of publication
1999
Pages
7589 - 7600
Database
ISI
SICI code
0040-4020(19990611)55:24<7589:AO2MTT>2.0.ZU;2-3
Abstract
The formal synthesis of benzyl 2,3-aziridino-N-(benzyloxycarbonyl)-2,3(21) from D-ribose is described. Reaction of 21 with excess benzyl alcohol in th e presence of boron trifluoride etherate and hydrogenolysis of the product gave (3S,4S)-dihydroxy-L-glutamic acid ((3S,4S)3). (C) 1999 Elsevier Scienc e Ltd. All rights reserved.