Stereoselective synthesis of imidazolidine, imidazoline and imidazole C- and N-pseudonucleosides

Authors
Fernandez-Bolanos, JG Zafra, E Lopez, O Robina, I Fuentes, J
Citation
Jg. Fernandez-bolanos et al., Stereoselective synthesis of imidazolidine, imidazoline and imidazole C- and N-pseudonucleosides, TETRAHEDR-A, 10(15), 1999, pp. 3011-3023
Citations number
31
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
15
Year of publication
1999
Pages
3011 - 3023
Database
ISI
SICI code
0957-4166(19990730)10:15<3011:SSOIIA>2.0.ZU;2-M
Abstract
Methyl 2-deoxy-2-isothiocyanato-alpha-D-glucopyranoside 2, which exists in equilibrium with the corresponding 2,3-cyclic carbamate 1, reacts with D-gl ucosamine producing the pseudo-C and N-nucleoside of chiral imidazolidine-2 -thione 3, in good yield and high stereoselectivity. Starting from 3, diffe rent pseudo-C- and N-nucleosides of imidazoline-2-thione 6-11, and of imida zole 12 and 13 are obtained. Conformational aspects of some of the prepared compounds are discussed. (C) 1999 Elsevier Science Ltd. All rights reserve d.