Enantiomeric d4T analogues and their structural determination

被引：15

作者：

Selouane, A

Vaccher, C

Villa, P

Postel, D

Len, C ^{[1
]}

机构：

[1] Univ Picardie, Lab Glucides, F-80039 Amiens, France

[2] Univ IBN Tofail, Kenitra, Morocco

[3] Univ Lille 2, Fac Sci Pharmaceut & Biol, Chim Analyt Lab, F-59006 Lille, France

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 04期

关键词：

D O I：

10.1016/S0957-4166(02)00106-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Asymmetric synthesis of d4T analogues having a benzo[c]furan moiety with two asymmetric carbon atoms was realized using Sharpless asymmetric dihydroxylation as the key step in a synthesis starting from o-phthalaldehyde. Enantiomeric purities were determined by analytical chiral HPLC with an amylose-derived stationary phase, while the absolute configurations were established by X-ray crystallography. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：407 / 413

页数：7

相关论文

共 23 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] New perspectives for the treatment of HIV infections [J].

De Clercq, E .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1998, 63 (04) :449-479

[7] TOWARD IMPROVED ANTI-HIV CHEMOTHERAPY - THERAPEUTIC STRATEGIES FOR INTERVENTION WITH HIV-INFECTIONS [J].

DECLERCQ, E .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (14) :2491-2517

[8] 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

[9] 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

[10] Asymmetric synthesis of both enantiomers of two acyclic nucleoside analogues related to d4T and acyclovir [J].

Ewing, DF ;

Glaçon, V ;

Mackenzie, G ;

Len, C .

TETRAHEDRON LETTERS, 2002, 43 (06) :989-991