Asymmetric synthesis of both enantiomers of two acyclic nucleoside analogues related to d4T and acyclovir

被引:13
作者
Ewing, DF
Glaçon, V
Mackenzie, G
Len, C
机构
[1] Univ Picardie Jules Verne, Lab Glucides, F-80039 Amiens, France
[2] Univ Hull, Dept Chem, Ctr Organ & Biol Chem, Kingston Upon Hull HU6 7RX, N Humberside, England
关键词
acyclic nucleosides; d4T acyclovir; asymmetric dihydroxylation;
D O I
10.1016/S0040-4039(01)02298-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The enantiomers of 1-{[(2-hydroxy-1-phenyl)ethoxy]methyl}thymine and 9-{[(2-hydroxy-1-phenyl)ethoxy]methyl}guanine have been obtained in high yield in live steps from (R)- and (S)-1-phenylethan-1,2-diol. These chiral compounds are acyclic nucleoside analogues of d4T and acyclovir, respectively. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:989 / 991
页数:3
相关论文
共 16 条
[1]  
AHLUWALIA G, 1986, BIOCHEM PHARMACOL, V35, P3797
[2]  
BALZARINI J, 1987, MOL PHARMACOL, V32, P162
[3]   (-)-2'-DEOXY-3'-THIACYTIDINE IS A POTENT, HIGHLY SELECTIVE INHIBITOR OF HUMAN-IMMUNODEFICIENCY-VIRUS TYPE-1 AND TYPE-2 REPLICATION INVITRO [J].
COATES, JAV ;
CAMMACK, N ;
JENKINSON, HJ ;
JOWETT, AJ ;
JOWETT, MI ;
PEARSON, BA ;
PENN, CR ;
ROUSE, PL ;
VINER, KC ;
CAMERON, JM .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1992, 36 (04) :733-739
[4]   INITIAL STUDIES ON THE CELLULAR PHARMACOLOGY OF 2',3'-DIDEOXYCYTIDINE, AN INHIBITOR OF HTLV-III INFECTIVITY [J].
COONEY, DA ;
DALAL, M ;
MITSUYA, H ;
MCMAHON, JB ;
NADKARNI, M ;
BALZARINI, J ;
BRODER, S ;
JOHNS, DG .
BIOCHEMICAL PHARMACOLOGY, 1986, 35 (13) :2065-2068
[5]   An efficient asymmetric approach to carbocyclic nucleosides: Asymmetric synthesis of 1592U89, a potent inhibitor of HIV reverse transcriptase [J].
Crimmins, MT ;
King, BW .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (13) :4192-4193
[6]   SELECTIVITY OF ACTION OF AN ANTI-HERPETIC AGENT, 9-(2-HYDROXYETHOXYMETHYL)GUANINE [J].
ELION, GB ;
FURMAN, PA ;
FYFE, JA ;
DEMIRANDA, P ;
BEAUCHAMP, L ;
SCHAEFFER, HJ .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1977, 74 (12) :5716-5720
[7]   Nucleoside analogues with a novel glycone based on the benzo[c]furan core [J].
Ewing, DF ;
Fahmi, NE ;
Len, C ;
Mackenzie, G ;
Ronco, G ;
Villa, P ;
Shaw, G .
NUCLEOSIDES & NUCLEOTIDES, 1999, 18 (11-12) :2613-2630
[8]   Stereoisomeric pyrimidine nucleoside analogues based on the 1,3-dihydrobenzo[c]furan core [J].
Ewing, DF ;
Fahmi, NE ;
Len, C ;
Mackenzie, G ;
Pranzo, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (21) :3561-3565
[9]   Facile separation of chiral 1,3-dihydrobenzo[c]furan derivatives using a D-xylose moiety as a protecting group [J].
Ewing, DF ;
Len, C ;
Mackenzie, G ;
Ronco, G ;
Villa, P .
TETRAHEDRON-ASYMMETRY, 2000, 11 (24) :4995-5002
[10]  
Ewing DF, 1996, COLLECT CZECH CHEM C, V61, pS145