IMPROVED SYNTHESIS OF (E)-2'-DEOXY-2'-(FLUOROMETHYLENE)CYTIDINE - A POTENT INHIBITOR OF RIBONUCLEOTIDE DIPHOSPHATE REDUCTASE

被引：29

作者：

MATTHEWS, DP

PERSICHETTI, RA

SABOL, JS

STEWART, KT

MCCARTHY, JR

机构：

[1] Marion Merrell Dow Research Institute, Cincinnati, 45215

来源：

NUCLEOSIDES & NUCLEOTIDES | 1993年 / 12卷 / 02期

关键词：

D O I：

10.1080/07328319308021198

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

An improved synthesis of 1 is reported that utilizes cytidine as starting material and incorporates the stereospecific method to fluoro olefins as in the original process. The new route is five steps, compared to the seven step original procedure, with an overall yield of 29%. Several intermediates are crystalline and readily purified.

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页码：115 / 123

页数：9

相关论文

共 12 条

[1] SEPARATION OF NUCLEOSIDE MIXTURES ON DOWEX-1(OH-) [J].

DEKKER, CA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (17) :4027-&

[2]

HOSMANE RS, 1981, SYNTHESIS-STUTTGART, V2, P118

[3] TETRA-TERT-BUTOXYDISILOXANE-1,3-DIYL, A NEW TYPE OF BIFUNCTIONAL SILYL PROTECTIVE GROUP [J].

MARKIEWICZ, WT ;

NOWAKOWSKA, B ;

ADRYCH, K .

TETRAHEDRON LETTERS, 1988, 29 (13) :1561-1564

[4] NUCLEOSIDES AND NUCLEOTIDES .97. SYNTHESIS OF NEW BROAD-SPECTRUM ANTINEOPLASTIC NUCLEOSIDES, 2'-DEOXY-2'-METHYLIDENECYTIDINE (DMDC) AND ITS DERIVATIVES [J].

MATSUDA, A ;

TAKENUKI, K ;

TANAKA, M ;

SASAKI, T ;

UEDA, T .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (02) :812-819

[5]

MATSUDA A, 1988, CHEM PHARM BULL, V36, P945

[6] STEREOSPECIFIC METHOD TO E-TERMINAL AND Z-TERMINAL FLUORO OLEFINS AND ITS APPLICATION TO THE SYNTHESIS OF 2'-DEOXY-2'-FLUOROMETHYLENE NUCLEOSIDES AS POTENTIAL INHIBITORS OF RIBONUCLEOSIDE DIPHOSPHATE REDUCTASE [J].

MCCARTHY, JR ;

MATTHEWS, DP ;

STEMERICK, DM ;

HUBER, EW ;

BEY, P ;

LIPPERT, BJ ;

SNYDER, RD ;

SUNKARA, PS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7439-7440

[7] A NEW ROUTE TO VINYL FLUORIDES [J].

MCCARTHY, JR ;

MATTHEWS, DP ;

EDWARDS, ML ;

STEMERICK, DM ;

JARVI, ET .

TETRAHEDRON LETTERS, 1990, 31 (38) :5449-5452

[8] ORGANOPHOSPHOROUS ANALOGS AND DERIVATIVES OF NUCLEOTIDES .1. PHOSPHONO AND METHYLPHOSPHINO ANALOGS OF AMINOACYL-5'-ADENILIC ACID [J].

NATCHEV, IA .

TETRAHEDRON, 1988, 44 (20) :6455-6463

[9]

STUBBE J, COMMUNICATION

[10]

SUNKARA SP, UNPUB