Synthesis of 2′,3′-dideoxy-3′,3′-difluoro and 2′,3′-dideoxy-2′,2′-difluoropyranosyl nucleosides analogues of gemcitabine

被引：17

作者：

Fernández, R ^{[1
]}

Castillón, S ^{[1
]}

机构：

[1] Univ Rovira & Virgili, Dept Quim Analit & Quim Organ, Tarragona 43005, Spain

来源：

TETRAHEDRON | 1999年 / 55卷 / 28期

关键词：

D O I：

10.1016/S0040-4020(99)00468-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The gem-difluoronucleosides 1 and 2, pyranosyl analogues of gemcitabine, have been synthesized from D-mannose and D-glucose respectively. The key steps were the formation of the difluoromethylene group by reaction of the corresponding ulose with DAST, and the glycosylation. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：8497 / 8508

页数：12

共 52 条

[1] SYNTHESIS AND INTERACTION WITH URIDINE PHOSPHORYLASE OF 5'-DEOXY-4',5-DIFLUOROURIDINE, A NEW PRODRUG OF 5-FLUOROURACIL [J].

AJMERA, S ;

BAPAT, AR ;

STEPHANIAN, E ;

DANENBERG, PV .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (06) :1094-1098

[2] A new promoter system for the sulfoxide glycosylation reaction [J].

Alonso, I ;

Khiar, N ;

MartinLomas, M .

TETRAHEDRON LETTERS, 1996, 37 (09) :1477-1480

[3] SYNTHESIS OF 2,4-DIDEOXY-BETA-D-ERYTHRO-HEXOPYRANOSYL NUCLEOSIDES [J].

AUGUSTYNS, K ;

ROZENSKI, J ;

VANAERSCHOT, A ;

JANSSEN, G ;

HERDEWIJN, P .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (11) :2977-2982

[4] ANTI-RETROVIRUS ACTIVITY OF 3'-FLUORO-SUBSTITUTED AND 3'-AZIDO-SUBSTITUTED PYRIMIDINE 2',3'-DIDEOXYNUCLEOSIDE ANALOGS [J].

BALZARINI, J ;

BABA, M ;

PAUWELS, R ;

HERDEWIJN, P ;

DECLERCO, E .

BIOCHEMICAL PHARMACOLOGY, 1988, 37 (14) :2847-2856

[5] An improved synthesis of 4-O-benzoyl-2,2-difluorooleandrose from L-rhamnose.: Factors determining the synthesis of 2,2-difluorocarbohydrates from 2-uloses [J].

Barrena, MI ;

Matheu, MI ;

Castillón, S .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (07) :2184-2188

[6] SNCL4 VERSUS TICL4-MEDIATED COUPLING BETWEEN N-6-BENZOYLADENINE AND PERBENZOYLATED 2-DEOXYPYRANOSE - APPLICATION TO THE SYNTHESIS OF CERTAIN HOMOCHIRAL ACYCLONUCLEOSIDES AND CARBOACYCLONUCLEOSIDES [J].

BAUD, MV ;

CHAVIS, C ;

LUCAS, M ;

IMBACH, JL .

TETRAHEDRON, 1991, 47 (48) :9993-10002

[7] FLUORINE SUBSTITUTED ANALOGS OF NUCLEOSIDES AND NUCLEOTIDES [J].

BERGSTROM, D ;

ROMO, E ;

SHUM, P .

NUCLEOSIDES & NUCLEOTIDES, 1987, 6 (1-2) :53-63

[8] SYNTHESIS OF UNSATURATED 4'-AZIDO PYRANOSYL THYMINES AS POTENTIAL ANTIVIRAL AND ANTI-HIV AGENTS [J].

BESSODES, M ;

EGRON, MJ ;

FILIPPI, J ;

ANTONAKIS, K .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (11) :3035-3039

[9] Trityl ethers in oligosaccharide synthesis: A novel strategy for the convergent assembly of oligosaccharides [J].

Boons, GJ ;

Bowers, S ;

Coe, DM .

TETRAHEDRON LETTERS, 1997, 38 (21) :3773-3776

[10]

Bunn PA, 1998, CLIN CANCER RES, V4, P1087

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