A GENERAL-METHOD FOR THE PREPARATION OF BENZYLIC ALPHA,ALPHA-DIFLUOROPHOSPHONIC ACIDS - NONHYDROLYZABLE MIMETICS OF PHOSPHOTYROSINE

被引：124

作者：

SMYTH, MS ^{[1
]}

FORD, H ^{[1
]}

BURKE, TR ^{[1
]}

机构：

[1] NCI, DIV CANC TREATMENT, DEV THERAPEUT PROGRAM, MED CHEM LAB, BETHESDA, MD 20892 USA

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 29期

关键词：

D O I：

10.1016/S0040-4039(00)74672-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Methodology is presented for the preparation of heretofore unreported benzylic alpha,alpha-difluorophosphonic acids. Oxidation of benzylic alpha-hydroxyphosphonates using MnO2 provided a new route for the synthesis of benzylic alpha-oxophosphonate, which were then fluorinated using DAST. Hydrolysis of ester protecting groups yielded alpha,alpha-difluorophosphonic acids. These represent non-hydrolyzable mimetics of arylphosphates which could be of value in the study of cellular phosphotyrosine-utilizing signal transduction pathways.

引用

页码：4137 / 4140

页数：4

共 19 条

[1] Albert A., 1962, IONIZATION CONSTANTS
[2] BLACKBURN GM, 1981, CHEM IND-LONDON, P134
[3] THE SYNTHESIS AND METAL-BINDING CHARACTERISTICS OF NOVEL, ISOPOLAR PHOSPHONATE ANALOGS OF NUCLEOTIDES
BLACKBURN, GM
KENT, DE
KOLKMANN, F
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (05): : 1119 - 1125
[4] BLACKBURN GM, 1986, J CHEM SOC P1, V1, P913
[5] BURKE T R JR, 1992, Drugs of the Future, V17, P119
[6] PHOSPHONATE-CONTAINING INHIBITORS OF TYROSINE-SPECIFIC PROTEIN-KINASES
BURKE, TR
LI, ZH
BOLEN, JB
MARQUEZ, VE
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (05) : 1577 - 1581
[7] TYROSINE KINASE AND CONTROL OF CELL-PROLIFERATION
COMOGLIO, PM
DIRENZO, MF
GAUDINO, G
PONZETTO, C
PRAT, M
[J]. AMERICAN REVIEW OF RESPIRATORY DISEASE, 1990, 142 (06): : S16 - S19
[8] DIFFERDING E, 1991, SYNLETT, P395
[9] Engel R., 1983, P97
[10] PROTEIN TYROSINE PHOSPHATASES - A DIVERSE FAMILY OF INTRACELLULAR AND TRANSMEMBRANE ENZYMES
FISCHER, EH
CHARBONNEAU, H
TONKS, NK
[J]. SCIENCE, 1991, 253 (5018) : 401 - 406

← 1 2 →