SYNTHESIS OF 2-FLUORO SUGAR AND ITS CONDENSATION REACTION WITH SILYLATED THYMINE

被引:7
作者
NIIHATA, S
EBATA, T
KAWAKAMI, H
MATSUSHITA, H
机构
[1] Life Science Research Laboratory, Japan Tabacco Inc., Aoba-ku, Yokohama, Kanagawa 227
关键词
D O I
10.1246/bcsj.68.1509
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
2,3-Dideoxy-2-fluoro-D-erythro-pentofuranose was easily prepared from 3-DPA lactone. The condensation reaction between 1-O-acetyl derivative of this sugar and silylated thymine in the presence of TMSOTf proceeded in a poorly stereoselective manner.
引用
收藏
页码:1509 / 1512
页数:4
相关论文
共 20 条
[11]   FURANOID GLYCAL AS A STARTING MATERIAL FOR NUCLEOSIDE DERIVATIVES [J].
KAWAKAMI, H ;
EBATA, T ;
KOSEKI, K ;
OKANO, K ;
MATSUMOTO, K ;
MATSUSHITA, H .
HETEROCYCLES, 1993, 36 (12) :2765-2776
[12]   ACID-STABLE 2'-FLUORO PURINE DIDEOXYNUCLEOSIDES AS ACTIVE AGENTS AGAINST HIV [J].
MARQUEZ, VE ;
TSENG, CKH ;
MITSUYA, H ;
AOKI, S ;
KELLEY, JA ;
FORD, H ;
ROTH, JS ;
BRODER, S ;
JOHNS, DG ;
DRISCOLL, JS .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (03) :978-985
[13]   SYNTHESIS OF (2S,4S)-2-HYDROXY-4-HYDROXYMETHYL-4-BUTANOLIDE, A HUNGER SUBSTANCE [J].
MATSUMOTO, K ;
EBATA, T ;
KOSEKI, K ;
KAWAKAMI, H ;
OKANO, K ;
MATSUSHITA, H .
HETEROCYCLES, 1992, 34 (02) :363-367
[14]   SYNTHESIS OF NUCLEOSIDES .9. GENERAL SYNTHESIS OF N-GLYCOSIDES .1. SYNTHESIS OF PYRIMIDINE NUCLEOSIDES [J].
NIEDBALLA, U ;
VORBRUGGEN, H .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (25) :3654-3660
[15]   SYNTHESIS OF 1-(2,3-DIDEOXY-2-FLUORO-BETA-D-THREO-PENTOFURANOSYL)CYTOSINE (F-DDC) - A PROMISING AGENT FOR THE TREATMENT OF ACQUIRED-IMMUNE-DEFICIENCY-SYNDROME [J].
OKABE, M ;
SUN, RC ;
ZENCHOFF, GB .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (14) :4392-4397
[16]   SYNTHESIS OF THE DIDEOXYNUCLEOSIDES DDC AND CNT FROM GLUTAMIC-ACID, RIBONOLACTONE, AND PYRIMIDINE-BASES [J].
OKABE, M ;
SUN, RC ;
TAM, SYK ;
TODARO, LJ ;
COFFEN, DL .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (20) :4780-4786
[17]   3'-FLUORO-2',3'-DIDEOXY-5-CHLOROURIDINE - MOST SELECTIVE ANTI-HIV-1 AGENT AMONG A SERIES OF NEW 2'-FLUORINATED AND 3'-FLUORINATED 2',3'-DIDEOXYNUCLEOSIDE ANALOGS [J].
VANAERSCHOT, A ;
HERDEWIJN, P ;
BALZARINI, J ;
PAUWELS, R ;
DECLERCQ, E .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (08) :1743-1749
[18]   NUCLEOSIDE SYNTHESES .22. NUCLEOSIDE SYNTHESIS WITH TRIMETHYLSILYL TRIFLATE AND PERCHLORATE AS CATALYSTS [J].
VORBRUGGEN, H ;
KROLIKIEWICZ, K ;
BENNUA, B .
CHEMISCHE BERICHTE-RECUEIL, 1981, 114 (04) :1234-1255
[19]   A GENERAL-METHOD FOR CONTROLLING GLYCOSYLATION STEREOCHEMISTRY IN THE SYNTHESIS OF 2'-DEOXYRIBOSE NUCLEOSIDES [J].
WILSON, LJ ;
LIOTTA, D .
TETRAHEDRON LETTERS, 1990, 31 (13) :1815-1818