New pyrophosphate analogues:: a facile access to N-(O-alkylsulfamoyl)phosphoramidic acids via a simple and quantitative reaction, of N-(O-alkylsulfamoyl)trimethylphospha-λ5-azene with bromotrimethylsilane and water

被引:3
作者
Bonnac, L [1 ]
Barragan, V [1 ]
Winum, JY [1 ]
Montero, JL [1 ]
机构
[1] Univ Montpellier 2, UMR 5032, ENSCM, Lab Chim Biomol, F-34296 Montpellier, France
关键词
alkylsulfamates; phosphorylation; pyrophosphate analogues;
D O I
10.1016/j.tet.2004.01.035
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new strategy to prepare pyrophosphate analogues through selective and quantitative cleavage of N-(O-alkylsulfamoyl)tri-alkylphospha-gimel5 -azene esters (R-O-SO2-N=P(OR')(3)) has been developed. Using pure bromotrimethylsilane, N-(O-alkyl-sulfamoyl)tris-trimethylsilylphospha-gimel(5)-azenes (R-O-SO2-N=P(OSiMe3)(3)) have been easily obtained as intermediates. N-(O-Alkyl-sulfamoyl)phosphoramidic acids (R-O-SO2-NH-P(O)(OH)(2)) have been formed quantitatively by hydrolysis of the silylated intermediates. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2187 / 2190
页数:4
相关论文
共 19 条
[1]  
Boudjabi S, 2000, SYNLETT, P716
[2]  
DECLERCQ E, 1987, ANTIVIR RES, V8, P261
[3]   A NOVEL SELECTIVE BROAD-SPECTRUM ANTI-DNA VIRUS AGENT [J].
DECLERCQ, E ;
HOLY, A ;
ROSENBERG, I ;
SAKUMA, T ;
BALZARINI, J ;
MAUDGAL, PC .
NATURE, 1986, 323 (6087) :464-467
[4]   AIDS-DRIVEN NUCLEOSIDE CHEMISTRY [J].
HURYN, DM ;
OKABE, M .
CHEMICAL REVIEWS, 1992, 92 (08) :1745-1768
[5]   SYNTHESIS OF ANALOGS OF 5-IODO-2'-DEOXYURIDINE-5'-DIPHOSPHATE [J].
JENNINGS, LJ ;
MACCHIA, M ;
PARKIN, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (17) :2197-2202
[6]  
LEVCHENKO ES, 1960, ZH OBSHCH KHIM+, V30, P1941
[7]  
MACCHIA M, 1994, FARMACO, V49, P325
[8]  
MARSMANN H, 1981, NMR-BASIC PRINC PROG, V17, P65
[9]  
MCKENNA CE, 1977, TETRAHEDRON LETT, P155
[10]  
MORITA CT, 1996, FORUM IMMUNOL, P347