Polyhydroxylated N-(thio)carbamoyl piperidines:: nojirimycin-type glycomimetics with controlled anomeric configuration

被引：15

作者：

García-Moreno, MI

Mellet, CO

Fernández, JMG

机构：

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

[2] CSIC, Inst Invest Quim, E-41092 Seville, Spain

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 22期

关键词：

D O I：

10.1016/S0957-4166(99)00462-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

N-(Thio)carbamoyl D-xylo-nojirimycin derivatives have been prepared by intramolecular rearrangement of sugar thiourea precursors under basic conditions. The stereochemistry at the aminoketal stereocentre is under stereoelectronic control, with the diastereomer having the pseudoanomeric group in axial orientation being obtained in all cases. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：4271 / 4275

页数：5

共 23 条

[1]

Babiano R., 1986, CARBOHYD RES, V154, P280

[2]

Blanco JLJ, 1997, CHEM COMMUN, P1969

[3] Tautomeric rearrangement of 3-deoxy-3-thioureidoaldoses: A novel synthetic route to carbohydrate mimics having a cyclic thiourea structure [J].