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
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
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收藏
页码:6759 / 6780
页数:22
相关论文
共 74 条
[1]   THIANTHRENE 5-OXIDE (SSO) AS A MECHANISTIC PROBE OF THE ELECTROPHILIC CHARACTER IN THE OXYGEN-TRANSFER BY DIOXIRANES [J].
ADAM, W ;
GOLSCH, D .
CHEMISCHE BERICHTE, 1994, 127 (06) :1111-1113
[2]   A CONVENIENT PREPARATION OF ACETONE SOLUTIONS OF DIMETHYLDIOXIRANE [J].
ADAM, W ;
BIALAS, J ;
HADJIARAPOGLOU, L .
CHEMISCHE BERICHTE, 1991, 124 (10) :2377-2377
[3]   EPOXIDATION VERSUS ALLYLIC OXIDATION (CH INSERTION) IN THE OXYFUNCTIONALIZATION OF VINYLSILANES AND BETA-HYDROXY DERIVATIVES BY DIMETHYLDIOXIRANE [J].
ADAM, W ;
PRECHTL, F ;
RICHTER, MJ ;
SMERZ, AK .
TETRAHEDRON LETTERS, 1995, 36 (28) :4991-4994
[4]   TRANSFORMATIONS OF PENICILLINS .4. TRAPPING OF SULFENIC ACIDS FROM PENICILLINS WITH THIOLS [J].
ALLAN, RD ;
BARTON, DHR ;
GIRIJAVALLABHAN, M ;
SAMMES, PG ;
TAYLOR, MV .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (11) :1182-1187
[5]   FORMATION AND REACTIONS OF SULFENIC ACIDS IN PROTEINS [J].
ALLISON, WS .
ACCOUNTS OF CHEMICAL RESEARCH, 1976, 9 (08) :293-299
[6]  
BARTON DHR, 1975, J CHEM SOC CHEM COMM, P557
[7]   RESEARCHES ON ANTIVIRAL AGENTS .31. SYNTHESIS AND TRANSFORMATIONS OF RACEMIC AND CHIRAL 6-OXIRANYL PYRIMIDINONES [J].
BOTTA, M ;
SALADINO, R ;
LAMBA, D ;
NICOLETTI, R .
TETRAHEDRON, 1993, 49 (27) :6053-6070
[8]   RESEARCHES ON ANTIVIRAL AGENTS .4. STUDIES ON THE CHEMISTRY OF 6-METHYL-2-METHOXY-4-O-ACYLOXY AND 6-METHYL-2,4-DI-O-ACYLOXYPYRIMIDINE DERIVATIVES AS NEW ACYLATION REAGENTS AND INHIBITORS OF URACIL DNA GLYCOSYLASES [J].
BOTTA, M ;
SALADINO, R ;
GENTILE, G ;
SUMMA, V ;
NICOLETTI, R ;
VERRI, A ;
FOCHER, F ;
SPADARI, S .
TETRAHEDRON, 1994, 50 (11) :3603-3618
[9]  
BOTTA M, 1994, MED CHEM RES, V4, P323
[10]   *UBER METHYLIERTE NUCLEOSIDE UND PURINE UND IHRE PHARMAKOLOGISCHEN WIRKUNGEN .1. METHYLIERUNG VON NUCLEOSIDEN DURCH DIAZOMETHAN [J].
BREDERECK, H .
CHEMISCHE BERICHTE-RECUEIL, 1947, 80 (05) :401-405