NUCLEIC ACID RELATED COMPOUNDS .73. FLUORINATION OF URIDINE 2'-THIOETHERS WITH XENON DIFLUORIDE OR (DIETHYLAMINO)SULFUR TRIFLUORIDE - SYNTHESIS OF STABLE 2'-[ALKYLSULFONYL]-2'-DEOXY-2'-FLUOROURIDINES OR 2'-[ARYLSULFONYL]-2'-DEOXY-2'-FLUOROURIDINES

被引：25

作者：

ROBINS, MJ ^{[1
]}

MULLAH, KB ^{[1
]}

WNUK, SF ^{[1
]}

DALLEY, NK ^{[1
]}

机构：

[1] UNIV ALBERTA,DEPT CHEM,EDMONTON T6G 2E1,ALBERTA,CANADA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 08期

关键词：

D O I：

10.1021/jo00034a031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of 2,2'-anhydro-1-beta-D-arabinofuranosyluracil with thiolate anions gave the 2'-S-alkyl(and aryl)-2'-thiouridines (1). Oxidation of 3',5'-di-O-acetyl-2'-S-alkyl(and aryl)-2'-thiouridines (2) with 3-chloroperoxybenzoic acid (MCPBA) gave the diastereomeric sulfoxides 4. Treatment of 2 with XeF2 or 4 with (diethylamino)sulfur trifluoride/SbCl3 gave the diastereomeric 3',5'-di-O-acetyl-2'-S-alkyl(and aryl)-2'-fluoro-2'-thiouridines (9). These alpha-fluoro thioethers were oxidized (MCPBA) to their stable sulfone derivatives 11 that are analogues of the biologically active 2'-deoxy-2',2'-difluoro nucleosides. Stereochemistry (2'S) and conformations of the major diastereomers were established by X-ray crystallography. Efficient conversions of 11 to the cytidine alpha-fluoro sulfones 14 were achieved.

引用

页码：2357 / 2364

页数：8

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