The synthesis of unsymmetrical S1-(3′-O-thymidine-O-methanephosphonyl)-S2-p-nitrophenyl disulfides and their reactions with triphenylphosphine

被引:2
作者
Chworos, A [1 ]
Wozniak, LA [1 ]
Stec, WJ [1 ]
机构
[1] Polish Acad Sci, Ctr Mol & Macromol Studies, Dept Bioorgan Chem, PL-90363 Lodz, Poland
关键词
nucleic acid analogues; phosphonic acids; derivatives; disulfides; stereoselectivity;
D O I
10.1016/S0040-4039(99)02247-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of thymidine 3'-methanephosphonothioic acid with p-nitrophenylsulfenyl chloride provides S-1 -(3'-O-thymidine-O-methanephosphonyl)-S-2-p-nitrophenyl disulfide which, in the presence of an excess of sulfenyl chloride and triphenylphosphine gives, in a stereospecific manner, thymidine 3'-(S-p-nitrophenyl methanephosphonodithioate). (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1219 / 1222
页数:4
相关论文
共 6 条
[1]   SYNTHESIS AND P-DIASTEREOMERIC RESOLUTION OF NUCLEOSIDE 3'-O(S-ALKYL) AND NUCLEOSIDE 3'-O(S-ARYL) METHYLPHOSPHONOTHIOATES [J].
BRILL, WKD ;
CARUTHERS, MH .
TETRAHEDRON LETTERS, 1988, 29 (11) :1227-1230
[2]  
HIGSON AP, 1993, J CHEM SOC P1, P1091
[3]  
HUDSON HR, 1990, CHEM ORGANOPHOSPHORU, V1, P448
[4]  
MUKAIYAMA T, 1976, TOPICS PHOSPHORUS CH, P587
[5]  
STEC WJ, 1997, ANTISENSE NUCLEIC A, V7, P383
[6]  
Wozniak LA, 1998, J ORG CHEM, V63, P9109