5'-O-benzoyl-2'-keto-3'-deoxy-alpha-uridine: First unambiguous synthesis, crystal structure and its use to establish the anomerisation of 2'-ketouridines under basic conditions.

被引：6

作者：

Sakthivel, K

Pathak, T

Suresh, CG

机构：

[1] NATL CHEM LAB,ORGAN CHEM DIV SYNTH,POONA 411008,MAHARASHTRA,INDIA

[2] NATL CHEM LAB,DIV BIOCHEM SCI,POONA 411008,MAHARASHTRA,INDIA

来源：

TETRAHEDRON | 1996年 / 52卷 / 05期

关键词：

D O I：

10.1016/0040-4020(95)01011-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

5'-O-benzoyl-3'-deoxy-2'-keto-alpha-uridine was characterised unambiguously with the help of crystal structure analysis and provided H-1-NMR data to differentiate it from its B-anomer. We have also established, with the help of the above H-1-NMR data that the earlier reported procedures (ref. 4,5) of synthesising 2'-ketouridine produced a mixture of anomers.

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页码：1767 / 1772

页数：6

相关论文

共 14 条

[1]

IWASAKI H, THESIS NAGOYA U JAPA

[2] FACILE TRANSFORMATION OF BETA-D-RIBOFURANOSYL PURINES AND PYRIMIDINES INTO THEIR RESPECTIVE 3'-DEOXY-THREO-PENTOFURANOSYL NUCLEOSIDES [J].

KAWANA, M ;

NISHIKAWA, M ;

YAMASAKI, N ;

KUZUHARA, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (09) :1593-1596

[3] SYNTHESIS OF FUSED CYCLOPROPANE-CONTAINING NUCLEOSIDES BY [1,2]-HYDRIDE SHIFT REARRANGEMENTS AND BETA-ELIMINATION REACTIONS OF SULFONYLATED RIBONUCLEOSIDES [J].

KAWANA, M ;

KUZUHARA, H .

NUCLEOSIDES & NUCLEOTIDES, 1992, 11 (2-4) :551-569

[4] SYNTHESES OF 2',3'-DIDEOXY-2'-METHYLENE PYRIMIDINE NUCLEOSIDES AS POTENTIAL ANTI-HUMAN-IMMUNODEFICIENCY-VIRUS (HIV) AGENTS [J].

LIN, TS ;

LUO, MZ ;

LIU, MC .

NUCLEOSIDES & NUCLEOTIDES, 1992, 11 (2-4) :329-340

[5]

MINAMOTO K, 1989, NUCL ACID S, V21, P121

[6]

MOTHERWELL WDS, 1978, PLUTO PROGRAM PLOTTI

[7] ONE-STEP SYNTHESIS OF C-2 DIALKYLAMINO-SUBSTITUTED 2',3'-O-ANHYDRO-LYXO-URIDINES - 1ST REPORT ON THE OPENING OF 2,2'-O-ANHYDRO-BRIDGE OF 2,2'-O-ANHYDROURIDINE BY SECONDARY-AMINES [J].

SAKTHIVEL, K ;

BERA, S ;

PATHAK, T .

TETRAHEDRON, 1993, 49 (45) :10387-10392

[8] REACTIONS OF DIMESYLTHYMIDINE WITH SECONDARY-AMINES - EASY ACCESS TO 3',5'-DIDEOXY-3'-SUBSTITUTED-5'-ALKYLAMINOTHYMIDINES - NEW CLASSES OF POTENTIAL ANTIVIRAL AMINONUCLEOSIDES [J].

SAKTHIVEL, K ;

KUMAR, RK ;

PATHAK, T .

TETRAHEDRON, 1993, 49 (20) :4365-4372

[9] REACTIONS OF 2',3'-DI-O-MESYL-LYXO-URIDINE WITH SECONDARY-AMINES - FIRST REPORT ON THE ONE-POT CONVERSION OF MESYLATED NUCLEOSIDES TO ENAMINONUCLEOSIDES AND THE CRYSTAL-STRUCTURE OF ALPHA-ENAMINE [J].

SAKTHIVEL, K ;

PATHAK, T ;

SURESH, CG .

TETRAHEDRON, 1994, 50 (46) :13251-13260

[10] SYNTHESIS OF 1-(3'-DEOXY-BETA-D-GLYCEROPENTOFURAN-2'-ULOSYL)URACIL BY SELECTIVE ELIMINATION-REACTIONS [J].

SASAKI, T ;

MINAMOTO, K ;

HATTORI, K .

TETRAHEDRON, 1974, 30 (16) :2689-2694