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

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1995年 / 68卷 / 05期

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

页码：1509 / 1512

页数：4

共 20 条

[1]

ABDELMEGIED AES, 1991, SYNTHESIS-STUTTGART, P313

[2]

AYE KA, 1988, CARBOHYD RES, V183, P261

[3] 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

[4] STEREOSELECTIVE SYNTHESIS OF 2',3'-DIDEOXY-NUCLEOSIDES AND 2,3'-DIDEHYDRO-2',3'-DIDEOXY-NUCLEOSIDES [J].

CHU, CK ;

BEACH, JW ;

BABU, JR ;

JEONG, LS ;

JEONG, HK ;

AHN, SK ;

ISLAM, Q ;

LEE, SJ ;

CHEN, YQ .

NUCLEOSIDES & NUCLEOTIDES, 1991, 10 (1-3) :423-426

[5] 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

[6] 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

[7]

Hudlicky M., 1988, ORG REACTIONS, V35, P513, DOI DOI 10.1002/0471264180.0R035.03

[8] STEREOSELECTIVITY IN THE COUPLING REACTION BETWEEN 2-PHENYLTHIO-2,3-DIDEOXYRIBOSE AND SILYLATED PYRIMIDINE-BASES [J].

KAWAKAMI, H ;

EBATA, T ;

KOSEKI, K ;

MATSUSHITA, H ;

NAOI, Y ;

ITOH, K .

CHEMISTRY LETTERS, 1990, (08) :1459-1462

[9] CONDENSATION REACTION BETWEEN 2,2-DIPHENYLTHIO-2,3-DIDEOXYRIBOSE AND SILYLATED PYRIMIDINE-BASES [J].

KAWAKAMI, H ;

EBATA, T ;

KOSEKI, K ;

MATSUMOTO, K ;

OKANO, K ;

MATSUSHITA, H .

NUCLEOSIDES & NUCLEOTIDES, 1992, 11 (09) :1673-1682

[10] SYNTHESIS OF 2',3'-DIDEHYDRO-2',3'-DIDEOXYNUCLEOSIDES UTILIZING COUPLING REACTIONS BETWEEN NUCLEIC BASES AND PHENYLTHIO-SUBSTITUTED 2,3-DIDEOXYRIBOSE [J].

KAWAKAMI, H ;

EBATA, T ;

KOSEKI, K ;

MATSUMOTO, K ;

MATSUSHITA, H ;

NAOI, Y ;

ITOH, K .

HETEROCYCLES, 1991, 32 (12) :2451-2470

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