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

被引：7

作者：

KAWANA, M

KUZUHARA, H

机构：

[1] RIKEN (The Institute of Physical and Chemical Research), Wako

来源：

NUCLEOSIDES & NUCLEOTIDES | 1992年 / 11卷 / 2-4期

关键词：

D O I：

10.1080/07328319208021725

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：

(1'R, 3'S and R, 5'S)-4'-Oxo-2'-oxabicyclo[3.1.0]hexan-3'-yl pyrimidines and purines were synthesized from ribonucleosides in 2-5 steps. The configurations of the base moieties in the cyclopropano keto-nucleosides were determined by NOE difference spectroscopy.

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页码：551 / 569

页数：19

相关论文

共 41 条

[1]

ADACHI T, 1977, J CHEM SOC CHEM COMM, P247

[2] ACYLATION OF 2',3',5'-TRI-O-ACETYLGUANOSINE [J].

BRIDSON, PK ;

MARKIEWICZ, WT ;

REESE, CB .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (21) :791-792

[3] A NOVEL ONE-FLASK CYCLOPROPANATION AND VINYLCYCLOPROPANATION METHOD FOR ALPHA-ENONES - COPPER(I)-INDUCED GAMMA-THIOPHENOXIDE REMOVAL FROM CONJUGATE ADDUCTS [J].

COHEN, T ;

MYERS, M .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (02) :457-460

[4] NEW CATALYSTS AND PROCEDURES FOR THE DIMETHOXYTRITYLATION AND SELECTIVE SILYLATION OF RIBONUCLEOSIDES [J].

HAKIMELAHI, GH ;

PROBA, ZA ;

OGILVIE, KK .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1982, 60 (09) :1106-1113

[5] NUCLEIC-ACID RELATED-COMPOUNDS .45. A DEOXYGENATIVE [1,2]-HYDRIDE SHIFT REARRANGEMENT CONVERTING CYCLIC CIS-DIOL MONOTOSYLATES TO INVERTED SECONDARY ALCOHOLS [J].

HANSSKE, F ;

ROBINS, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (22) :6736-6737

[6]

HARAGUCHI K, 1990, NUCL ACID S, V22, P3

[7] REACTION OF ADENINE NUCLEOSIDES, TOSYLATED IN THE CARBOHYDRATE MOIETY, WITH LITHIUM TRIETHYLBOROHYDRIDE [J].

HERDEWIJN, P .

TETRAHEDRON, 1989, 45 (20) :6563-6580

[8]

HILDESHEIM J, 1970, CHEM IND-LONDON, P94

[9]

IKEHARA M, 1974, YUKI GOSEI KAGAKU KA, V32, P402

[10] SYNTHESIS AND NUCLEAR MAGNETIC RESONANCE SPECTRUM OF 3',4',6'-TRIO-O-ACETYL-2-(METHYLTHIO)-D-GLUCOPYRANO[2',1'.4,5]-2-THIAZOLINE [J].

ITO, T .

CANADIAN JOURNAL OF CHEMISTRY, 1966, 44 (01) :94-&

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