Synthesis of 2′,3′-dideoxy-2′-monofluoromethyI azanucleosides

被引：25

作者：

Qiu, XL

Qing, FL

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China

[2] Donghua Univ, Coll Chem & Chem Engn, Shanghai 200051, Peoples R China

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2005年 / 13卷 / 01期

关键词：

azanucleosides; fluorinated compounds;

D O I：

10.1016/j/bmc.2004.09.040

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：

(2S,4S)-Methyl-N-tert-butoxycarbonyl-4-monofluoromethylpyroglutamate 6 was synthesized via a key dehydrofluorination followed by hydrogenation. Compound 6 was converted to (5S,3S)-N-benzyloxycarbonyl-5-tert-butyldimethylsilyloxymethyl-3-monofluoromethyl-2-pyrrolidone 12 over four steps in 62% yield, which was used as a precursor for the synthesis of 2',3'-dideoxy-2'-monofluoromethyl azanucleosides 17-18. (C) 2004 Elsevier Ltd. All rights reserved.

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收藏

页码：277 / 283

页数：7

相关论文

共 25 条

[1] SYNTHESIS OF CARBOCYCLIC NUCLEOSIDES [J].

AGROFOGLIO, L ;

SUHAS, E ;

FARESE, A ;

CONDOM, R ;

CHALLAND, SR ;

EARL, RA ;

GUEDJ, R .

TETRAHEDRON, 1994, 50 (36) :10611-10670

[2]

BERGSTROM DE, 1988, FLUORINE CONTAINING, P259

[3] SYNTHESIS OF CHIRAL CARBOCYCLIC NUCLEOSIDES [J].

BORTHWICK, AD ;

BIGGADIKE, K .

TETRAHEDRON, 1992, 48 (04) :571-623

[4] USE OF 2'-FLUORO-5-METHYL-BETA-L-ARABINOFURANOSYLURACIL AS A NOVEL ANTIVIRAL AGENT FOR HEPATITIS-B VIRUS AND EPSTEIN-BARR-VIRUS [J].

CHU, CK ;

MA, TW ;

SHANHMUGANATHAN, K ;

WANG, CG ;

XIANG, YJ ;

PAI, SB ;

YAO, GQ ;

SOMMADOSSI, JP ;

CHENG, YC .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1995, 39 (04) :979-981

[5] New developments in the enantioselective synthesis of cyclopentyl carbocyclic nucleosides [J].

Crimmins, MT .

TETRAHEDRON, 1998, 54 (32) :9229-9272

[6] NUCLEOSIDES OF FLUORO SUGARS .6. SYNTHESIS AND REACTIVITY OF 3'-FLUORO-3'-DESOXYTHYMIDINE AND 3'-CHLORO-3'-DESOXYTHYMIDINE [J].

ETZOLD, G ;

HINTSCHE, R ;

KOWOLLIK, G ;

LANGEN, P .

TETRAHEDRON, 1971, 27 (12) :2463-&

[7] Biocatalytic selective modifications of conventional nucleosides, carbocyclic nucleosides, and C-nucleosides [J].

Ferrero, M ;

Gotor, V .

CHEMICAL REVIEWS, 2000, 100 (12) :4319-+

[8] SYNTHESIS OF NUCLEOSIDES FLUORINATED IN THE SUGAR MOIETY - THE APPLICATION OF DIETHYLAMINOSULFUR TRIFLUORIDE TO THE SYNTHESIS OF FLUORINATED NUCLEOSIDES [J].

HERDEWIJN, P ;

VANAERSCHOT, A ;

KERREMANS, L .

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 1989, 8 (01) :65-96

[9] Sugar-modified nucleosides in past 10 years, a review [J].

Ichikawa, E ;

Kato, K .

CURRENT MEDICINAL CHEMISTRY, 2001, 8 (04) :385-423

[10] Structure-activity relationships of 2'-deoxy-2',2'-difluoro-L-erythro-pentofuranosyl nucleosides [J].

Kotra, LP ;

Xiang, YJ ;

Newton, MG ;

Schinazi, RF ;

Cheng, YC ;

Chu, CK .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (22) :3635-3644