RAPID SYNTHESIS OF 2',3'-DIDEOXYCYTIDINE (DDC) FROM A SIMPLE ACHIRAL PRECURSOR

被引：15

作者：

JUNG, ME

CASTRO, C

GARDINER, JM

机构：

[1] Department of Chemistry and Biochemistry, University of California, Los Angeles

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 41期

关键词：

D O I：

10.1016/S0040-4039(00)93538-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The antiviral nucleoside analogue, 2',3'-dideoxycytidine (ddC) 1, has been synthesized in nine steps and good overall yield from crotonaldehyde 2 via the chiral epoxy alcohol 4 prepared by a Sharpless epoxidation.

引用

页码：5717 / 5720

页数：4

共 16 条

[1] PHARMACODYNAMICS OF 2',3'-DIDEOXYCYTIDINE - AN INHIBITOR OF HUMAN-IMMUNODEFICIENCY-VIRUS [J].

BRODER, S .

AMERICAN JOURNAL OF MEDICINE, 1990, 88 (5B) :S2-S7

[2] A NEW SYNTHESIS OF 2',3'-DIDEOXYNUCLEOSIDES FOR AIDS CHEMOTHERAPY [J].

FARINA, V ;

BENIGNI, DA .

TETRAHEDRON LETTERS, 1988, 29 (11) :1239-1242

[3] THE ANTIVIRAL ACTIVITY OF DIDEOXYCYTIDINE [J].

JEFFRIES, DJ .

JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY, 1989, 23 :29-34

[4] SYNTHETIC APPROACHES TO 3'-AZIDO-3'-DEOXYTHYMIDINE AND OTHER MODIFIED NUCLEOSIDES [J].

JUNG, ME ;

GARDINER, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (08) :2614-2615

[5] PREPARATION OF MODIFIED NUCLEOSIDES FROM GLUCOSAMINE - RAPID AND EFFICIENT FORMAL TOTAL SYNTHESIS OF SEVERAL 2'-DEOXY C-NUCLEOSIDES [J].

JUNG, ME ;

TRIFUNOVICH, ID ;

GARDINER, JM ;

CLEVENGER, GL .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (01) :84-85

[6]

JUNG ME, UNPUB J ORG CHEM

[7]

JUNG ME, 1991, J AM CHEM SOC, V113, P5117

[8] ANOMERIC DEOXY AND UNSATURATED METHYL PENTOFURANOSIDES AND PENTOPYRANOSIDES [J].

LEMIEUX, RU ;

WATANABE, KA ;

PAVIA, AA .

CANADIAN JOURNAL OF CHEMISTRY, 1969, 47 (23) :4413-&

[9]

MANSURI MM, 1987, ANNU REP MED CHEM, V22, P147

[10] PREPARATION OF THE GEOMETRIC ISOMERS OF DDC, DDA, D4C AND D4T AS POTENTIAL ANTI-HIV AGENTS [J].

MANSURI, MM ;

FARINA, V ;

STARRETT, JE ;

BENIGNI, DA ;

BRANKOVAN, V ;

MARTIN, JC .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1991, 1 (01) :65-68

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