IOOC route to substituted chiral pyrrolidines. Potential glycosidase inhibitors

Authors
Falb, E Bechor, Y Nudelman, A Hassner, A Albeck, A Gottlieb, HE
Citation
E. Falb et al., IOOC route to substituted chiral pyrrolidines. Potential glycosidase inhibitors, J ORG CHEM, 64(2), 1999, pp. 498-506
Citations number
57
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
64
Issue
2
Year of publication
1999
Pages
498 - 506
Database
ISI
SICI code
0022-3263(19990122)64:2<498:IRTSCP>2.0.ZU;2-W
Abstract
Branched-chain five-membered ring aza-sugar analogues, synthesized from ami no acids by an intramolecular oxime-olefin cycloaddition reaction, the IOOC route, were found to be selective glycosidase inhibitors. The derivative 2 ,4(S)-di(hydroxymethyl)-3(S)-aminopyrrolidine, obtained from D-serine, was about 1 order of potency more active than its enantiomer obtained from L-se rine.