SYNTHESIS OF THE THYMIDINE BUILDING-BLOCKS FOR A NONHYDROLYZABLE DNA ANALOG

被引：14

作者：

KAWAI, SH ^{[1
]}

WANG, DG ^{[1
]}

JUST, G ^{[1
]}

机构：

[1] MCGILL UNIV,DEPT CHEM,MONTREAL H3A 2K6,QUEBEC,CANADA

来源：

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 1992年 / 70卷 / 05期

关键词：

D O I：

10.1139/v92-193

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The 3'-deoxy-3'-C-(2''-hydroxyethyl)thymidine derivatives 4 and 13 were efficiently synthesized from either thymidine via a known 3'-radical allylation, or from the branched-chain furanose 5 involving the removal of the 2'-hydroxyl after stereospecific nucleosidation. The 5'-deoxy-5'-thiothymidine 20 was prepared via a regiospecific Mitsunobu coupling, providing the third unit required for the synthesis of sulfide-linked DNA analogues.

引用

收藏

页码：1573 / 1580

页数：8

相关论文

共 50 条

[41] BUILDING-BLOCKS FOR GLYCOPEPTIDE SYNTHESIS - DISACCHARIDE GLYCOSYL ISOTHIOCYANATES [J].

MELLET, CO ;

BLANCO, JLJ ;

FERNANDEZ, JMG ;

FUENTES, J .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1993, 12 (4-5) :487-505

[42] PREPARATION OF CHIRAL BUILDING-BLOCKS FOR STARBURST DENDRIMER SYNTHESIS [J].

LAPIERRE, JM ;

SKOBRIDIS, K ;

SEEBACH, D .

HELVETICA CHIMICA ACTA, 1993, 76 (07) :2419-2432

[43] TOTAL SYNTHESES WITH TRICYCLOOCTANONE BUILDING-BLOCKS - SYNTHESIS OF IRIDODIAL [J].

RITTERSKAMP, P ;

DEMUTH, M ;

SCHAFFNER, K .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (07) :1155-1158

[44] SYNTHESIS OF FUNCTIONALIZED RING-A BUILDING-BLOCKS FOR TAXOIDS [J].

TJEPKEMA, MW ;

WILSON, PD ;

WONG, T ;

ROMERO, MA ;

AUDRAIN, H ;

FALLIS, AG .

TETRAHEDRON LETTERS, 1995, 36 (34) :6039-6042

[45] SMALL CARBORANES AS BUILDING-BLOCKS IN DESIGNED ORGANOMETALLIC SYNTHESIS [J].

GRIMES, RN .

PURE AND APPLIED CHEMISTRY, 1991, 63 (03) :369-372

[46] FUNCTIONALIZED NITROALKANES AS USEFUL BUILDING-BLOCKS IN SYNTHESIS OF PHEROMONES [J].

ROSINI, G .

ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1988, 195 :35-AGRO

[47] EFFICIENT ASYMMETRIC-SYNTHESIS OF INDOLIZIDINE BUILDING-BLOCKS [J].

BOND, TJ ;

JENKINS, R ;

RIDLEY, AC ;

TAYLOR, PC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (19) :2241-2242

[48] Oxazolines - Chiral building-blocks for synthesis, auxiliaries and ligands [J].

不详 .

NACHRICHTEN AUS CHEMIE TECHNIK UND LABORATORIUM, 1996, 44 (7-8) :744-&

[49] BADGE - A SYNTHESIS TOOL FOR CUSTOMIZED ARITHMETIC BUILDING-BLOCKS [J].

MUNZNER, A .

IFIP TRANSACTIONS A-COMPUTER SCIENCE AND TECHNOLOGY, 1993, 22 :373-384

[50] LACTONES AS BUILDING-BLOCKS FOR SYNTHESIS OF ALKALOID LIKE HETEROCYCLES [J].

ZYMALKOWSKI, F ;

MEISE, W .

HETEROCYCLES, 1978, 9 (10) :1474-1475

← 1 2 3 4 5 →