THE SYNTHESIS OF ISOPRENOID (PHOSPHINYLMETHYL)PHOSPHONATES

被引：48
作者：
BILLER, SA
FORSTER, C
机构：
来源：
TETRAHEDRON | 1990年 / 46卷 / 19期
关键词：
D O I：
10.1016/S0040-4020(01)87856-X
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A synthetic route to isoprenoid (phosphinylmethyl)phosphonates (PMPs), stable analogues of the biologically important diphosphates, is described. This method involves the reaction of an α-phosphonate carbanion with an isoprenoid phosphonochloridate to provide the PMP triesters, followed by ester cleavage with TMSBr or TMSI. 13C NMR, 31P NMR, 19F NMR and FAB-MS data were employed for the characterization of PMP salts and triesters. © 1990.
引用
收藏
页码：6645 / 6658
页数：14
相关论文
共 31 条
[1]   2-MERCAPTOBENZOTHIAZOLE - AN IMPROVED REAGENT FOR THE REMOVAL OF METHYL PHOSPHATE PROTECTING GROUPS FROM OLIGODEOXYNUCLEOTIDE PHOSPHOTRIESTERS [J].
ANDRUS, A ;
BEAUCAGE, SL .
TETRAHEDRON LETTERS, 1988, 29 (43) :5479-5482
[2]   ALPHA-DIAZOPHOSPHONIC ACIDS AS POTENTIAL PHOTOAFFINITY-LABELING REAGENTS - SYNTHESIS, STABILITY, AND PHOTOCHEMISTRY [J].
BARTLETT, PA ;
CARRUTHERS, NI ;
WINTER, BM ;
LONG, KP .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (07) :1284-1291
[3]   THE MICHAELIS-ARBUZOV REARRANGEMENT [J].
BHATTACHARYA, AK ;
THYAGARAJAN, G .
CHEMICAL REVIEWS, 1981, 81 (04) :415-430
[4]   EXPEDIENT AND HIGH-YIELD SYNTHESIS OF ALKYLPHOSPHONYL DICHLORIDES UNDER MILD, NEUTRAL CONDITIONS - REACTION OF BIS(TRIMETHYLSILYL)ALKYL PHOSPHONATES WITH OXALYL CHLORIDE DIMETHYLFORMAMIDE [J].
BHONGLE, NN ;
NOTTER, RH ;
TURCOTTE, JG .
SYNTHETIC COMMUNICATIONS, 1987, 17 (09) :1071-1076
[5]   ISOPRENOID (PHOSPHINYLMETHYL)PHOSPHONATES AS INHIBITORS OF SQUALENE SYNTHETASE [J].
BILLER, SA ;
FORSTER, C ;
GORDON, EM ;
HARRITY, T ;
SCOTT, WA ;
CIOSEK, CP .
JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (10) :1869-1871
[6]   THE DEALKYLATION OF PHOSPHATE AND PHOSPHONATE ESTERS BY IODOTRIMETHYLSILANE - A MILD AND SELECTIVE PROCEDURE [J].
BLACKBURN, GM ;
INGLESON, D .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (05) :1150-1153
[7]  
CLARKSTILL W, 1978, J ORG CHEM, V43, P2923
[8]   APPLICATION OF UNREACTIVE ANALOGS OF TERPENOID PYROPHOSPHATES TO STUDIES OF MULTISTEP BIOSYNTHESIS - DEMONSTRATION THAT PRESQUALENE PYROPHOSPHATE IS AN ESSENTIAL INTERMEDIATE ON PATH TO SQUALENE [J].
COREY, EJ ;
VOLANTE, RP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (05) :1291-1293
[9]   SYNTHESIS OF OLEFINS FROM O,O'-DIALKYL ALPHA-LITHIOALKYLPHOSPHONOTHIOATE ESTERS [J].
COREY, EJ ;
KWIATKOW.GT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (23) :5654-&
[10]   NEGATIVE-ION FAST ATOM BOMBARDMENT MASS-SPECTROMETRY OF ISOPRENOID DIPHOSPHATES AND RELATED ANALOGS [J].
DAVISSON, VJ ;
SHARP, TR ;
POULTER, CD .
BIOORGANIC CHEMISTRY, 1988, 16 (02) :111-123
1234