Transformations of thiopyrimidine and thiopurine nucleosides following oxidation with dimethyldioxirane.

被引：29

作者：

Saladino, R

Mincione, E

Crestini, C

Mezzetti, M

机构：

[1] Dipto. Agrochimico Agrobiologico, Univ. Studi di Viterbo La Tuscia, 01100 Viterbo, via San Camillo de Lellis

来源：

TETRAHEDRON | 1996年 / 52卷 / 19期

关键词：

D O I：

10.1016/0040-4020(96)00289-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general and convenient method for the synthesis of several pyrimidine and purine nucleosides by selective oxidation of thionucleosides with dimethyldioxirane is reported. Thioketo moieties in the C-4 position of the pyrimidine ring, and in the C-6, and C-8 positions of the purine ring are the domain of oxidative nucleophilic substitution. Thioketo moieties in the C-2 position of both purine and pyrimidine rings are the domain of desulfurization or formation of disulfides. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：6759 / 6780

页数：22

共 74 条

[61]

SUNG WL, 1987, J CHEM SOC CHEM COMM, P1089

[62]

VERHEYDEN JP, 1971, J ORG CHEM, V36, P250

[63]

VINKLER E, 1960, ACTA CHIM HUNG, V22, P345

[64] NUCLEOSIDE SYNTHESES .25. A NEW SIMPLIFIED NUCLEOSIDE SYNTHESIS [J].

VORBRUGGEN, H ;

BENNUA, B .

CHEMISCHE BERICHTE-RECUEIL, 1981, 114 (04) :1279-1286

[65]

WALTER W, 1966, LIEBIGS ANN CHEM, V698, P122

[66]

ZABICKY J, 1970, CHEM AMIDES, P449

[67] PYRIDYL GROUPS FOR PROTECTION OF THE IMIDE FUNCTIONS OF URIDINE AND GUANOSINE - EXPLORATION OF THEIR DISPLACEMENT-REACTIONS FOR SITE-SPECIFIC MODIFICATIONS OF URACIL AND GUANINE BASES [J].

ZHOU, XX ;

WELCH, CJ ;

CHATTOPADHYAYA, J .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1986, 40 (10) :806-816

[68]

ZIFF EB, 1968, J AM CHEM SOC, V26, P7338

[69]

Zorbach W. W, 1968, SYNTHETIC PROCEDURES, V1

[70]

ZWANENBURG B, 1970, RECL TRAV CHIM PAY-B, V89, P687

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