INTRODUCTION OF AN ALKYL GROUP INTO THE SUGAR PORTION OF URACILNUCLEOSIDES BY THE USE OF GILMAN REAGENTS

被引:6
作者
HAYAKAWA, H [1 ]
ASHIZAWA, H [1 ]
TANAKA, H [1 ]
MIYASAKA, T [1 ]
机构
[1] SHOWA UNIV, SCH PHARMACEUT SCI, HATANODAI 1-5-8, SHINAGAWA KU, TOKYO 142, JAPAN
关键词
C-alkylated dideoxyuridine nucleophilic substitution; organometallic reagent Gilman reagent uracilnucleoside 5'-alkyl-5'-deoxyuridine;
D O I
10.1248/cpb.38.355
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Substitution of a p-toluenesulfonyloxy group in the sugar portion of uracilnucleosides by an alkyl group was investigated by using Gilman reagents (R2CuLi). In the cases of S'-O-tosyl derivatives of 2/,3'-0-isopropylideneuridine, moderate yields of 5'-aIkylated products were obtained. In contrast to this, the reactions of the corresponding 2'-deoxyuridine derivatives gave higher yields of products. A similar substitution reaction at the 3'-position of 2'-deoxyuridine derivatives was also examined. © 1990, The Pharmaceutical Society of Japan. All rights reserved.
引用
收藏
页码:355 / 360
页数:6
相关论文
共 21 条
[1]   THE SYNTHESIS OF SOME BRANCHED-CHAIN-SUGAR NUCLEOSIDE ANALOGS [J].
ASHWELL, M ;
JONES, AS ;
WALKER, RT .
NUCLEIC ACIDS RESEARCH, 1987, 15 (05) :2157-2166
[2]  
BERRTZ SH, 1987, TETRAHEDRON LETT, V28, P4251
[3]   EVIDENCE FOR A REVERSIBLE D,PI-STAR-COMPLEXATION, BETA-CUPRATION SEQUENCE IN THE CONJUGATE ADDITION-REACTION OF GILMAN REAGENTS WITH ALPHA-ENONES, BETA-ENONES [J].
COREY, EJ ;
BOAZ, NW .
TETRAHEDRON LETTERS, 1985, 26 (49) :6015-6018
[4]  
ETZOLD G, 1968, J CHEM SOC CHEM COMM, P422
[5]  
HAYAKAWA H, 1985, TETRAHEDRON, V41, P1675, DOI 10.1016/S0040-4020(01)96481-6
[6]   A SIMPLE AND GENERAL ENTRY TO 5-SUBSTITUTED URIDINES BASED ON THE REGIOSELECTIVE LITHIATION CONTROLLED BY A PROTECTING GROUP IN THE SUGAR MOIETY [J].
HAYAKAWA, H ;
TANAKA, H ;
OBI, K ;
ITOH, M ;
MIYASAKA, T .
TETRAHEDRON LETTERS, 1987, 28 (01) :87-90
[7]  
HAYAKAWA H, 1987, CHEM PHARM BULL, V35, P72
[8]  
HAYAKAWA H, 1987, CHEM PHARM BULL, V35, P2605
[9]   REACTIONS OF LITHIUM DIORGANOCUPRATES(I) WITH TOSYLATES .2. STEREOCHEMICAL, KINETIC, AND MECHANISTIC ASPECTS [J].
JOHNSON, CR ;
DUTRA, GA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (23) :7783-7788
[10]   CHEMISTRY OF HIGHER-ORDER, MIXED ORGANOCUPRATES .1. SUBSTITUTION-REACTIONS AT UNACTIVATED SECONDARY CENTERS [J].
LIPSHUTZ, BH ;
WILHELM, RS ;
FLOYD, DM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (25) :7672-7674