NUCLEOSIDES .113. SYNTHESIS OF "6-(BETA-D-RIBOFURANOSYL)PYRIMIDINES - NEW CLASS OF PYRIMIDINE C-NUCLEOSIDES

被引：49

作者：

TAM, SYK ^{[1
]}

KLEIN, RS ^{[1
]}

DELASHERAS, FG ^{[1
]}

FOX, JJ ^{[1
]}

机构：

[1] CORNELL UNIV,SLOAN KETTERING DIV GRAD SCH MED SCI,SLOAN KETTERING INST,NEW YORK,NY 10021

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 26期

关键词：

D O I：

10.1021/jo00394a024

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of several 6-(α-D-ribofuranosyl)pyrimidines, a new class of C-nucleosides, from ethyl 3-(2, 3-0-isopropylidene-5-0-trityl-α-D-ribofuranosyl)propynoate (1) is described. Reaction of 1 with guanidine readily afforded 2-amino-4-oxopyrimidine 3. The 2-thio-4-oxopyrimidine derivative 18 was prepared via enamine 16 obtained by the addition of pyrrolidine to 1. Hydrolysis of 16 to αketo ester 17 and cyclization with thiourea afforded 18, which serves as the synthetic precursor of C-6 ribosyl-2-thiouracil 19, uracil 26, 4-thiouracil 29, and cytosine 31. © 1979, American Chemical Society. All rights reserved.

引用

页码：4854 / 4862

页数：9

共 50 条

[1] C-GLYCOSYL NUCLEOSIDES .2. FACILE SYNTHESIS OF DERIVATIVES OF 2,5-ANHYDRO-D-ALLOSE [J].

ALBRECHT, HP ;

REPKE, DB ;

MOFFATT, JG .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (10) :1836-1840

[2] C-GLYCOSYL NUCLEOSIDES .4. SYNTHESES OF SEVERAL 4-(BETA-D-RIBOFURANOSYL)PYRAZOLES [J].

ALBRECHT, HP ;

REPKE, DB ;

MOFFATT, JG .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (15) :2176-2182

[3]

Bellamy L.J, 1958, INFRA RED SPECTRA CO, Vsecond

[4] RESEARCHES ON ACETYLENIC COMPOUNDS .9. HETEROCYCLIC COMPOUNDS DERIVED FROM ETHYNYL KETONES [J].

BOWDEN, K ;

JONES, ERH .

JOURNAL OF THE CHEMICAL SOCIETY, 1946, (OCT) :953-954

[5]

Brown Daniel R.L., 2009, IACR CRYPTOL EPRINT, V2009, P620

[6]

BROWN DJ, 1970, PYRIMIDINES S1

[7]

BURCHENAL JH, 1976, CANCER RES, V36, P1520

[8] PREPARATION OF 1,3-THIAZINES . SULPHUR ANALOGUES OF NUCLEIC ACID PYRIMIDINE BASES [J].

CAIN, EN ;

WARRENER, RN .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1970, 23 (01) :51-+

[9]

Chambers R W, 1966, Prog Nucleic Acid Res Mol Biol, V5, P349, DOI 10.1016/S0079-6603(08)60240-8

[10] NUCLEOSIDES .100. GENERAL SYNTHESIS OF PYRIMIDINE C-5 NUCLEOSIDES RELATED TO PSEUDOURIDINE - SYNTHESIS OF "5-(BETA-D-RIBOFURANOSYL)ISOCYTOSINE (PSEUDOISOCYTIDINE), 5-(BETA-D-RIBOFURANOSYL)-2-THIOURACIL (2-THIOPSEUDOURIDINE) AND 5-(BETA-D-RIBOFURANOSYL)URACIL (PSEUDOURIDINE) [J].

CHU, CK ;

WEMPEN, I ;

WATANABE, KA ;

FOX, JJ .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (17) :2793-2797

← 1 2 3 4 5 →