SYNTHESIS OF ANTIVIRAL NUCLEOSIDES FROM CROTONALDEHYDE .3. TOTAL SYNTHESIS OF DIDEHYDRODIDEOXYTHYMIDINE (D4T)

被引:13
作者
JUNG, ME
GARDINER, JM
机构
[1] Department of Chemistry and Biochemistry, University of California Los Angeles, Los Angeles
基金
英国惠康基金; 美国国家卫生研究院;
关键词
D O I
10.1016/S0040-4039(00)74799-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The total synthesis of the antiviral agent d4T 3 from the epoxyalcohol 2, itself derived from crotonaldehyde 1, in 6 steps and 18% overall yield is described.
引用
收藏
页码:3841 / 3844
页数:4
相关论文
共 28 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 GENERAL SYNTHETIC METHOD FOR 2',3'-DIDEOXYNUCLEOSIDES - TOTAL SYNTHETIC APPROACH [J].
CHU, CK ;
RAGHAVACHARI, R ;
BEACH, JW ;
KOSUGI, Y ;
ULLAS, GV .
NUCLEOSIDES & NUCLEOTIDES, 1989, 8 (5-6) :903-906
[3]   A HIGHLY STEREOSELECTIVE GLYCOSYLATION OF 2-(PHENYLSELENENYL)-2,3-DIDEOXYRIBOSE DERIVATIVE WITH THYMINE - SYNTHESIS OF 3'-DEOXY-2',3'-DIDEHYDROTHYMIDINE AND 3'-DEOXYTHYMIDINE [J].
CHU, CK ;
BABU, JR ;
BEACH, JW ;
AHN, SK ;
HUANG, HQ ;
JEONG, LS ;
LEE, SJ .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (05) :1418-1420
[4]  
HANAMOTO Y, 1987, ANTIMICROB AGENTS CH, V31, P907
[5]  
HARAGUCHI K, 1991, J ORG CHEM, V56, P5402
[6]   CELLULAR PHARMACOLOGY OF 2',3'-DIDEOXY-2',3'-DIDEHYDROTHYMIDINE, A NUCLEOSIDE ANALOG ACTIVE AGAINST HUMAN IMMUNODEFICIENCY VIRUS [J].
HO, HT ;
HITCHCOCK, MJM .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1989, 33 (06) :844-849
[7]   THE ANTIVIRAL ACTIVITY OF DIDEOXYCYTIDINE [J].
JEFFRIES, DJ .
JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY, 1989, 23 :29-34
[8]   RAPID SYNTHESIS OF 2',3'-DIDEOXYCYTIDINE (DDC) FROM A SIMPLE ACHIRAL PRECURSOR [J].
JUNG, ME ;
CASTRO, C ;
GARDINER, JM .
TETRAHEDRON LETTERS, 1991, 32 (41) :5717-5720
[9]   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
[10]   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