Facile synthesis of 2',3'-unsaturated nucleosides from 2-deoxyribose

被引:10
作者
Sujino, K [1 ]
Yoshida, T [1 ]
Sugimura, H [1 ]
机构
[1] NOGUCHI INST,ITABASHI KU,TOKYO 173,JAPAN
关键词
D O I
10.1016/0040-4039(96)01293-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A straightforward approach for the synthesis of 2',3'-unsaturated nucleosides starting from 2-deoxyribose is described. This novel route involves two new methods; (1) preparation of 2-deoxy-1-thioribofuranoside by direct condensation of 2-deoxyribose and thiophenol, (2) formation of the nucleoside skeleton by the direct coupling of 2,3-unsaturated 1-thiopentofuranoside with pyrimidine bases. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:6133 / 6136
页数:4
相关论文
共 35 条
[1]  
ABDELMEGIED AES, 1991, SYNTHESIS-STUTTGART, P313
[2]   AN UNUSUALLY FACILE [3,3]-SIGMATROPIC REARRANGEMENT IN A STEREOSPECIFIC SYNTHESIS OF NOVEL 2',3'-DIDEOXYNUCLEOSIDE PRECURSORS [J].
ARMSTRONG, PL ;
COULL, IC ;
HEWSON, AT ;
SLATER, MJ .
TETRAHEDRON LETTERS, 1995, 36 (24) :4311-4314
[3]  
BALZARINI J, 1987, MOL PHARMACOL, V32, P162
[4]   A HIGHLY STEREOSELECTIVE SYNTHESIS OF ANTI-HIV 2',3'-DIDEOXYNUCLEOSIDES AND 2',3'-DIDEHYDRO-2',3'-DIDEOXYNUCLEOSIDES [J].
BEACH, JW ;
KIM, HO ;
JEONG, LS ;
NAMPALLI, S ;
ISLAM, Q ;
AHN, SK ;
BABU, JR ;
CHU, CK .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (14) :3887-3894
[5]   EFFICIENT TRANSFORMATION OF THYMIDINE INTO 2',3'-DIDEHYDRO-2',3'-DIDEOXY-THYMIDINE (D4T) INVOLVING OPENING OF A 2,3'-ANHYDRO DERIVATIVE BY PHENYLSELENOL [J].
BECOUARN, S ;
CZERNECKI, S ;
VALERY, JM .
NUCLEOSIDES & NUCLEOTIDES, 1995, 14 (06) :1227-1232
[6]   5'-BENZOYL-2'ALPHA-BROMO-3'-O-METHANESULFONYLTHYMIDINE - A SUPERIOR NUCLEOSIDE FOR THE SYNTHESIS OF THE ANTI-AIDS DRUG D4T (STAVUDINE) [J].
CHEN, BC ;
QUINLAN, SL ;
STARK, DR ;
REID, JG ;
AUDIA, VH ;
GEORGE, JG ;
EISENREICH, E ;
BRUNDIDGE, SP ;
RACHA, S ;
SPECTOR, RH .
TETRAHEDRON LETTERS, 1995, 36 (44) :7957-7960
[7]   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
[8]   A SHORT SYNTHESIS OF 2',3'-DIDEHYDRO-3'-DEOXYTHYMIDINE [J].
COSFORD, NDP ;
SCHINAZI, RF .
NUCLEOSIDES & NUCLEOTIDES, 1993, 12 (02) :149-155
[9]   SYNTHESIS OF ETHYL AND PHENYL 1-THIO-1,2-TRANS-D-GLYCOPYRANOSIDES FROM THE CORRESPONDING PER-O-ACETYLATED GLYCOPYRANOSES HAVING A 1,2-TRANS-CONFIGURATION USING ANHYDROUS FERRIC-CHLORIDE AS A PROMOTER [J].
DASGUPTA, F ;
GAREGG, PJ .
ACTA CHEMICA SCANDINAVICA, 1989, 43 (05) :471-475
[10]   SYNTHESIS OF 1,2-TRANS-RELATED 1-THIOGLYCOSIDE ESTERS [J].
FERRIER, RJ ;
FURNEAUX, RH .
CARBOHYDRATE RESEARCH, 1976, 52 (DEC) :63-68