PREPARATION AND PROPERTIES OF 2-DEOXYGLYCOSYL ISOTHIOCYANATES

被引：18

作者：

FUENTES, J

PRADERA, MA

ROBINA, I

机构：

[1] Departamento de Química Organica. Facultad

来源：

TETRAHEDRON | 1991年 / 47卷 / 30期

关键词：

GLYCOSYL ISOTHIOCYANATES; 2-DEOXY SUGARS; 2-DEOXY NUCLEOSIDES; GLYCOSYLTHIOUREAS; IMIDAZOLINE-2-THIONES;

D O I：

10.1016/S0040-4020(01)86530-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The syntheses of 3,4,6-tri-O-acetyl-2- deoxy-alpha and beta-D-arabino (D-lyxo)hexopyranosyl isothiocyanates (2, 3, 6, 7) and 4,6-di-O-acetyl-3-bromo-2,3-dideoxy-beta-D-arabinohexopyranosyl isothiocyanate (5) are reported. Treatments of 2,3,6, and 7 with phenacylamine hydrochloride and of 2 with aminoacetone hydrochloride gave the corresponding N-phenacyl (acetylmethyl)-N'-(2-deoxyglycosyl)-thioureas (8-12). The N-nucleoside analogues 5-methyl-1-(3',4',6'-tri-O- acetyl-2'-deoxy-alpha-D-arabinohexopyranosyl)-4-imidazoline-2-thione (13) was obtained by cyclodehydration of the thiourea 12.

引用

页码：5797 / 5810

页数：14

共 21 条

[1] REDUCTION OF ISOTHIOCYANATES TO THIOFORMAMIDES WITH TRI-NORMAL-BUTYLTIN HYDRIDE [J].