THE SYNTHESIS OF 2'-DEOXY-5-TRIFLUOROMETHYLURIDINE UTILIZING A COUPLING REACTION

被引：12

作者：

KAWAKAMI, H ^{[1
]}

EBATA, T ^{[1
]}

KOSEKI, K ^{[1
]}

MATSUSHITA, H ^{[1
]}

NAOI, Y ^{[1
]}

ITOH, K ^{[1
]}

MIZUTANI, N ^{[1
]}

机构：

[1] YUKI GOSEI KOGYO LTD,TOKYO RES LAB,ITABASHI KU,TOKYO 174,JAPAN

来源：

HETEROCYCLES | 1990年 / 31卷 / 03期

关键词：

D O I：

10.3987/COM-90-5315

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The coupling reaction between 1-α-chloro-2-deoxyribose derivative and silylated 5-trifluoromethyluracil was examined. The best stereoselectivity was obtained when the reaction was carried out using a large amount of silylated base in the presence of anhydrous zinc chloride. © 1990.

引用

页码：569 / 574

页数：6

共 18 条

[1] STEREOSELECTIVE SYNTHESIS OF ANOMERS OF 5-SUBSTITUTED 2'-DEOXYURIDINES [J].

AOYAMA, H .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (06) :2073-2077

[2]

HEIDELBERGER C, 1964, CANCER RES, V24, P1979

[3] SYNTHESES OF 5-TRIFLUOROMETHYLURACIL + 5-TRIFLUOROMETHYL-2-DEOXYURIDINE [J].

HEIDELBERGER, C ;

PARSONS, DG ;

REMY, DC .

JOURNAL OF MEDICINAL CHEMISTRY, 1964, 7 (01) :1-+

[4] SYNTHESES OF 5-TRIFLUOROMETHYLURACIL AND 5-TRIFLUOROMETHYL-2'-DEOXYURIDINE [J].

HEIDELBERGER, C ;

PARSONS, D ;

REMY, DC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (18) :3597-&

[5]

HEIN L, 1976, Patent No. 119423

[6] AN INVESTIGATION BY H-1-NMR SPECTROSCOPY INTO THE FACTORS DETERMINING THE BETA-ALPHA RATIO OF THE PRODUCT IN 2'-DEOXYNUCLEOSIDE SYNTHESIS [J].

HUBBARD, AJ ;

JONES, AS ;

WALKER, RT .

NUCLEIC ACIDS RESEARCH, 1984, 12 (17) :6827-6837

[7] THERAPEUTIC ANTIVIRAL ACTION OF 5-TRIFLUOROMETHYL-2]-DEOXYURIDINE IN HERPES SIMPLEX KERATITIS [J].

KAUFMAN, HE ;

HEIDELBERGER, C .

SCIENCE, 1964, 145 (363) :585-&

[8] THE SYNTHESIS OF 2'-DEOXYADENOSINE VIA STEREOSPECIFIC COUPLING REACTION [J].

KAWAKAMI, H ;

MATSUSHITA, H ;

NAOI, Y ;

ITOH, K ;

YOSHIKOSHI, H .

CHEMISTRY LETTERS, 1989, (02) :235-238

[9] STEREOSELECTIVITIES IN THE COUPLING REACTIONS BETWEEN 2-DEOXYRIBOSE DERIVATIVE AND SILYLATED ADENINE [J].

KAWAKAMI, H ;

MATSUSHITA, H ;

SHIBAGAKI, M ;

NAOI, Y ;

ITOH, K ;

YOSHIKOSHI, H .

CHEMISTRY LETTERS, 1989, (08) :1365-1368

[10] STUDIES ON ORGANIC FLUORINE-COMPOUNDS .35. TRIFLUOROMETHYLATION OF PYRIMIDINE-NUCLEOSIDES AND PURINE-NUCLEOSIDES WITH TRIFLUOROMETHYL-COPPER COMPLEX [J].

KOBAYASHI, Y ;

YAMAMOTO, K ;

ASAI, T ;

NAKANO, M ;

KUMADAKI, I .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (12) :2755-2761

← 1 2 →