A convenient synthesis of N-4,O-3',O-5'-triacetyl-2'-ketocytidine

被引：3

作者：

Kjell, DP

Slattery, BJ

机构：

[1] Lilly Research Laboratories, Eli Lilly and Co., Lafayette, IN 47902

来源：

NUCLEOSIDES & NUCLEOTIDES | 1997年 / 16卷 / 04期

关键词：

D O I：

10.1080/07328319708001363

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：

A convenient synthesis of the title compound in four steps from cytidine is reported. Key transformations include differentiation of the 2' position as N-4, O-3', O-5'-triacetyl-2,2'-anhydrocytidine, opening to the arabino derivative, and oxidation of the 2' position with the Dess-Martin reagent.

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收藏

页码：469 / 474

页数：6

相关论文

共 14 条

[1] KETONUCLEOSIDES [J].

ANTONAKIS, K .

ADVANCES IN CARBOHYDRATE CHEMISTRY AND BIOCHEMISTRY, 1984, 42 :227-264

[2] 3',3'-DIFLUORO-3'-DEOXYTHYMIDINE - COMPARISON OF ANTI-HIV ACTIVITY TO 3'-FLUORO-3'-DEOXYTHYMIDINE [J].

BERGSTROM, DE ;

MOTT, AW ;

DECLERCQ, E ;

BALZARINI, J ;

SWARTLING, DJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (18) :3369-3372

[3] CARBODIIMIDE-SULFOXIDE REACTIONS .9. SYNTHESIS OF 2'-KETO AND 3'-DERIVATIVES OF CYTIDINE [J].

BRODBECK, U ;

MOFFATT, JG .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (10) :3552-&

[4] 2'-O-NITRO-1-BETA-D-ARABINOFURANOSYLCYTOSINE - A NEW DERIVATIVE OF 1-BETA-D-ARABINOFURANOSYLCYTOSINE THAT RESISTS ENZYMATIC DEAMINATION AND HAS ANTI-LEUKEMIC ACTIVITY [J].

CHWANG, TL ;

FRIDLAND, A ;

AVERY, TL .

JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (02) :280-283

[5] CARBODIIMIDE-SULFOXIDE REACTIONS .6. SYNTHESES OF 2'- AND 3'-KETOURIDINES [J].

COOK, AF ;

MOFFATT, JG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (11) :2697-&

[6] NUCLEIC-ACID RELATED-COMPOUNDS .43. A CONVENIENT PROCEDURE FOR THE SYNTHESIS OF 2' AND 3'-KETONUCLEOSIDES [J].

HANSSKE, F ;

ROBINS, MJ .

TETRAHEDRON LETTERS, 1983, 24 (15) :1589-1592

[7] NUCLEIC-ACID RELATED-COMPOUNDS .44. 2' AND 3'-KETONUCLEOSIDES AND THEIR ARABINO AND XYLO REDUCTION PRODUCTS - CONVENIENT ACCESS VIA SELECTIVE PROTECTION AND OXIDATION OF RIBONUCLEOSIDES [J].

HANSSKE, F ;

MADEJ, D ;

ROBINS, MJ .

TETRAHEDRON, 1984, 40 (01) :125-135

[8] AN IMPROVED PROCEDURE FOR THE PREPARATION OF THE DESS-MARTIN PERIODINANE [J].

IRELAND, RE ;

LIU, LB .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (10) :2899-2899

[9] STUDIES ON BIOLOGICALLY-ACTIVE NUCLEOSIDES AND NUCLEOTIDES .2. CONVENIENT ONE-STEP SYNTHESIS OF 2,2'-ANHYDRO-1-(3',5'-DI-OMICRON-ACYL-BETA-D-ARABINOFURANOSYL)PYRIMIDINES FROM PYRIMIDINE RIBONUCLEOSIDES [J].

KONDO, K ;

INOUE, I .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (17) :2809-2812

[10] STUDIES ON BIOLOGICALLY-ACTIVE NUCLEOSIDES AND NUCLEOTIDES .7. SYNTHESIS OF SOME N4-ACYL AND N4-ACYLAMINOMETHYL 2,2'-ANHYDRONUCLEOSIDES [J].

KONDO, K ;

INOUE, I .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (09) :1577-1581