GENERAL AND EFFICIENT ROUTE TO PHOSPHORODITHIOATE ANALOGS OF NATURALLY-OCCURRING LIPIDS

被引:20
作者
MARTIN, SF
WAGMAN, AS
机构
[1] Department of Chemistry and Biochemistry, The University of Texas, Austin
关键词
D O I
10.1021/jo00074a012
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A general procedure has been developed for the efficient synthesis of lipid phosphorodithioate analogues 14a-f from 2-alkoxy-2-thio-1,3,2-dithiaphospholanes 13a-c, which are readily prepared from 2-chloro-1,3,2-dithiaphospholane (11) by sequential reaction with an alcohol and elemental sulfur.
引用
收藏
页码:5897 / 5899
页数:3
相关论文
共 53 条
[11]   SYNTHESIS OF DINUCLEOSIDE PHOSPHORODITHIOATES VIA THIOAMIDITES [J].
BRILL, WKD ;
NIELSEN, J ;
CARUTHERS, MH .
TETRAHEDRON LETTERS, 1988, 29 (43) :5517-5520
[12]   PHOSPHOLIPIDS CHIRAL AT PHOSPHORUS - STEREOCHEMICAL MECHANISM FOR THE FORMATION OF INOSITOL 1-PHOSPHATE CATALYZED BY PHOSPHATIDYLINOSITOL-SPECIFIC PHOSPHOLIPASE-C [J].
BRUZIK, KS ;
MOROCHO, AM ;
JHON, DY ;
RHEE, SG ;
TSAI, MD .
BIOCHEMISTRY, 1992, 31 (22) :5183-5193
[13]   FLUORINE IN ENZYME CHEMISTRY .2. THE PREPARATION OF DIFLUOROMETHYLENEPHOSPHONATE ANALOGS OF GLYCOLYTIC PHOSPHATES - APPROACHING AN ISOSTERIC AND ISOELECTRONIC PHOSPHATE MIMIC [J].
CHAMBERS, RD ;
JAOUHARI, R ;
OHAGAN, D .
TETRAHEDRON, 1989, 45 (16) :5101-5108
[14]   DEOXYNUCLEOSIDE PHOSPHORODITHIOATES - PREPARATION BY A TRIESTER METHOD [J].
DAHL, BH ;
BJERGARDE, K ;
NIELSEN, J ;
DAHL, O .
TETRAHEDRON LETTERS, 1990, 31 (24) :3489-3492
[15]   SYNTHETIC APPROACHES TO OLIGODEOXYRIBONUCLEOSIDE PHOSPHORODITHIOATES USING TERVALENT PHOSPHORUS MONOMERS [J].
DAHL, BH ;
BJERGARDE, K ;
SOMMER, VB ;
DAHL, O .
NUCLEOSIDES & NUCLEOTIDES, 1989, 8 (5-6) :1023-1027
[16]   DEOXYRIBONUCLEOSIDE PHOSPHORODITHIOATES - PREPARATION OF DINUCLEOSIDE PHOSPHORODITHIOATES FROM NUCLEOSIDE THIOPHOSPHORAMIDITES [J].
DAHL, BH ;
BJERGARDE, K ;
SOMMER, VB ;
DAHL, O .
ACTA CHEMICA SCANDINAVICA, 1989, 43 (09) :896-901
[17]  
DREEF CE, 1990, SYNLETT, P481
[18]   PHOSPHOROTHIOATE ANALOGS OF NUCLEOTIDES [J].
ECKSTEIN, F .
ACCOUNTS OF CHEMICAL RESEARCH, 1979, 12 (06) :204-210
[19]  
EKSTEIN F, 1979, ACCOUNTS CHEM RES, V12, P204
[20]  
Engel R., 1983, ROLE PHOSPHONATES LI, P93