THE SYNTHESIS OF SOME 5-SUBSTITUTED-6-AZA-2'-DEOXYURIDINES

被引：6

作者：

BASNAK, I ^{[1
]}

COE, PL ^{[1
]}

WALKER, RT ^{[1
]}

机构：

[1] UNIV BIRMINGHAM,SCH CHEM,BIRMINGHAM B15 2TT,ENGLAND

来源：

NUCLEOSIDES & NUCLEOTIDES | 1994年 / 13卷 / 1-3期

关键词：

D O I：

10.1080/15257779408013233

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 [生物化学与分子生物学]; 081704 [应用化学];

摘要：

5-(2-Thienyl)-1-(2-deoxy-3,5-di-O-p-toluoyl-beta-D-erythro-pentofuranosyl)-6-azauracil [VIII] and 5-cyclopropyl-1-(2-deoxy-3,5-di-O-p-toluoyl-beta-D-erythro-pentofuranosyl)-6-azauracil [X] were obtained in high yields (93.5% and 81.3% respectively) exclusively as beta anomers, by condensation of the corresponding silylated triazine bases with 2-deoxy-3,5-di-O-p-toluoyl-D-erythro-pentosyl chloride in chloroform. After deblocking both nucleosides with sodium methoxide in methanol, 5-(2-thienyl)-6-aza-2'-deoxyuridine [IX] and 5-cyclopropyl-6-aza-2'-deoxyuridine [XI] were obtained. The nucleoside IX was further acetylated, brominated with Br-2/CCl4 and deblocked with methanolic ammonia to give 6-aza-5[2-(5-bromothienyl)]-2'-deoxyuridine [XIV].

引用

页码：163 / 175

页数：13

共 18 条

[1]

NUCLEIC-ACID COMPONENTS AND THEIR ANALOGUES .174. SYNTHESIS OF 5-CYCLOPROPYL-6-AZAURACIL [J].