INTRODUCTION OF FLUORINE INTO THE C8 POSITION OF PURINE NUCLEOSIDES

被引：13

作者：

RATSEP, PC ^{[1
]}

ROBINS, RK ^{[1
]}

VAGHEFI, MM ^{[1
]}

机构：

[1] ICN,NUCL ACID RES INST,3300 HYLAND AVE,COSTA MESA,CA 92626

来源：

NUCLEOSIDES & NUCLEOTIDES | 1990年 / 9卷 / 02期

关键词：

D O I：

10.1080/07328319008045132

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

We have synthesized 2-amino-6,8-difluoro-9-(2,3,5-tri-0-acetyl- B-D-ribofuranosyl)purine (3) from 2-amino-6,8-dichloro-9-(2,3,5-tn-O-acetyl- B-D-ribofuranosyl)purine (1) in a two-step procedure. The reaction of 3 with anhydrous ammonia in dry 1,2-dimethoxyethane gave 2,8-diamino-6-fluoro-9-(2,3,5-tri-0-acetyl-S-D-ribofuranosyl)purine (4) in 64,1% yield. Compound 4 was deaminated with t-butylnitrite in tetrahydrofuran to give 2-amino-6-fluoro-9-(2,3,5-tri-0-acetyl-B-D-ribofuranosyl)purine (6). The 1H, 19F, and 13C NMR spectral data were determined and evaluated for each of the compounds. © 1990, Taylor & Francis Group, LLC. All rights reserved.

引用

页码：197 / 204

页数：8

共 27 条

[1] SYNTHESIS OF 6-FLUORO-9-METHYLPURINE [J].

BEAMAN, AG ;

ROBINS, RK .

JOURNAL OF MEDICINAL & PHARMACEUTICAL CHEMISTRY, 1962, 5 (06) :1067-&

[2]

BEAMAN AG, 1963, J ORG CHEM, V28, P2310

[3]

GERSTER JF, 1963, J MED CHEM, V6, P340

[4] PURINE NUCLEOSIDES .19. SYNTHESIS OF CERTAIN 8-CHLOROPURINE NUCLEOSIDES AND RELATED DERIVATIVES [J].

GERSTER, JF ;

HINSHAW, BC ;

ROBINS, RK ;

TOWNSEND, LB .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (03) :1070-&

[5] PURINE NUCLEOSIDES .X. SYNTHESIS OF CERTAIN NATURALLY OCCURRING 2-SUBSTITUTED AMINO-9-BETA-D-RIBOFURANOSYLPURIN-6(1H)-ONES (N2-SUBSTITUTED GUANOSINES) [J].

GERSTER, JF ;

ROBINS, RK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (16) :3752-&

[6] PURINE NUCLEOSIDES .13. SYNTHESIS OF 2-FLUORO- AND 2-CHLOROINOSINE AND CERTAIN DERIVED PURINE NUCLEOSIDES [J].

GERSTER, JF ;

ROBINS, RK .

JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (10) :3258-&

[7] NEW ANHYDROUS FLUORINATING SYSTEMS - THE COMBINATION OF CROWN-ETHERS AND CESIUM FLUORIDE - A RELATIVE RATE STUDY [J].

GINGRAS, M ;

HARPP, DN .

TETRAHEDRON LETTERS, 1988, 29 (37) :4669-4672

[8]

HEIDELBE.C, 1970, CANCER RES, V30, P1549

[9]

Heidelberger C, 1965, Prog Nucleic Acid Res Mol Biol, V4, P1, DOI 10.1016/S0079-6603(08)60783-7

[10]

IKEHARA M, 1971, CHEM PHARM BULL, V19, P104

← 1 2 3 →