Synthesis of 2-deoxy-3,5-di-O-benzoyl-2,2-difluoro-D-ribose from D-glucose and D-mannose.: A formal synthesis of gemcitabine

被引：24

作者：

Fernández, R ^{[1
]}

Matheu, MI ^{[1
]}

Echarri, R ^{[1
]}

Castillón, S ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 1998年 / 54卷 / 14期

关键词：

D O I：

10.1016/S0040-4020(98)00086-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The title compound 2-Deoxy-3,5-di-O-benzoyl-2,2-difluoro-D-ribose (17), was synthesised from D-glucose and from D-mannose. The key steps of the synthesis from D-glucose are obtaining the 3,3-difluoropyranose 9 by reacting the ulose 7 with DAST. and their conversion into the difluorofuranoside 17 by a degradative reaction of diol 16. Starting from D-mannose the synthesis obtains the 3,3-difluoroglycal 22 by reaction of the ulose 18 with DAST and oxidation-elimination of selenoglycoside 21. Ozonolysis of 22 gives the difluorofuranose 17. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：3523 / 3532

页数：10

共 27 条

[1] 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

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

BERGSTROM, D ;

ROMO, E ;

SHUM, P .

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

[3]

CHOU TS, 1992, SYNTHESIS-STUTTGART, P565

[4] CHEMOENZYMATIC SYNTHESES OF FLUORO SUGAR PHOSPHATES AND ANALOGS [J].

DRUECKHAMMER, DG ;

WONG, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) :5912-5913

[5] GEM-DIFLUORINATION VERSUS 1,2-MIGRATION AND FRAGMENTATION IN THE REACTION OF 2-ULOSES AND 3-ULOSES WITH DAST - INFLUENCE OF STEREOCHEMISTRY AT THE ANOMERIC CARBON-ATOM [J].

ELLAGHDACH, A ;

ECHARRI, R ;

MATHEU, MI ;

BARRENA, MI ;

CASTILLON, S ;

GARCIA, J .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (14) :4556-4559

[6] METHYL 5-O-TERT-BUTYLDIPHENYLSILYL-2-DEOXY-ALPHA,BETA-D-THREO-PENTOFURANOSIDE AS A DIVERGENT INTERMEDIATE FOR THE SYNTHESIS OF 3'-SUBSTITUTED-2',3'-DIDEOXYNUCLEOSIDES - SYNTHESIS OF 3'-AZIDO-3'-DEOXYTHYMIDINE, 3'-DEOXY-3'-FLUOROTHYMIDINE AND 3'-CYANO-3'-DEOXYTHYMIDINE [J].

FLEET, GWJ ;

SON, JC ;

DEROME, AE .

TETRAHEDRON, 1988, 44 (02) :625-636

[7]

GRINDEY GB, 1986, P AM ASSOC CANC RES, V27, P296

[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]

HERDEWIJN P, 1990, J MED CHEM, V33, P2150

[10]

HERSCOVIC J, 1982, SYNTHESIS-STUTTGART, P1967

← 1 2 3 →