SYNTHESIS OF SOME NOVEL 1-(5-THIO-BETA-D-XYLOPYRANOSYL)-LUMAZINE AND PYRIMIDINE NUCLEOSIDES

被引：10

作者：

ALMASOUDI, NA ^{[1
]}

PFLEIDERER, W ^{[1
]}

机构：

[1] UNIV CONSTANCE,FAK CHEM,W-7750 CONSTANCE,GERMANY

来源：

TETRAHEDRON | 1993年 / 49卷 / 34期

关键词：

D O I：

10.1016/S0040-4020(01)87232-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,2,3,4-Tetra-0-acetyl-5-thio-D-xylopyranose (1) reacts with the silylated lumazine bases (2-5) under trimethylsilyl trifluoromethylsulfonate catalysis to give the nucleosides 6, 8, 10, and 12 respectively, which face deblocking with potassium carbonate in dry methanol to yield the free nucleosides 7, 9, 11, and 13 respectively. The synthesis of 1-(2,3,4-tri-O-acetyl-5-thio-beta-xylopyranosyl)-thymine (17) and its free nucleoside 18 have been improved and in a similar manner reacted the silylated pyrimidine bases 15 and 16 to the 5-iodo- (19) and 5-fluoro- (21) analogues. Deacylation afforded the free nucleosides 20 and 22, respectively.

引用

页码：7579 / 7592

页数：14

共 34 条

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