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

被引：18

作者：

Fernández-Bolaños, JG ^{[1
]}

Zafra, E ^{[1
]}

López, O ^{[1
]}

Robina, I ^{[1
]}

Fuentes, J ^{[1
]}

机构：

[1] Univ Sevilla, Fac Quim, Dept Quim Organ, E-41071 Seville, Spain

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 15期

关键词：

D O I：

10.1016/S0957-4166(99)00314-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Methyl 2-deoxy-2-isothiocyanato-alpha-D-glucopyranoside 2, which exists in equilibrium with the corresponding 2,3-cyclic carbamate 1, reacts with D-glucosamine producing the pseudo-C and N-nucleoside of chiral imidazolidine-2-thione 3, in good yield and high stereoselectivity. Starting from 3, different pseudo-C- and N-nucleosides of imidazoline-2-thione 6-11, and of imidazole 12 and 13 are obtained. Conformational aspects of some of the prepared compounds are discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：3011 / 3023

页数：13

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