Acyclic C-nucleosides: synthesis of chiral 1,1-diheteroaryl-alditols and X-ray crystal structure of 2,3,5-tri-O-benzyl-1,1-di-(2'-pyrryl)-1-deoxy-D-arabinitol

被引:9
作者
Cornia, M
Capacchi, S
DelPogetto, M
Pelosi, G
Fava, GG
机构
[1] UNIV PARMA,CNR,DIPARTIMENTO CHIM GEN & INORGAN CHIM ANALIT CHIM,I-43100 PARMA,ITALY
[2] UNIV PARMA,CNR,CTR STUDIO STRUTTURIST DIFFRATTOMETR,I-43100 PARMA,ITALY
关键词
D O I
10.1016/S0957-4166(97)00328-5
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Tetra-O-acetyl-D-ribose, penta-O-acetyl-o-glucose, 2,3;5,6-di-O-isopropylidene-D-mannofuranose, 2,3,5-tri-O-benzyl-D-arabinofuranose and 2,3,5,6-tetra-O-benzyl-D-glucose react with pyrrole and indole, in presence of Lewis acids, to afford C-glycosylpyrroles and indoles in position 2 and 3 respectively (acyclic C-nucleosides, 1-7). The crystal structure of 4 was determined by X-ray crystallography. (C) 1997 Published by Elsevier Science Ltd.
引用
收藏
页码:2905 / 2912
页数:8
相关论文
共 37 条
[1]   SIR92 - a program for automatic solution of crystal structures by direct methods [J].
ALTOMARE, A ;
CASCARANO, G ;
GIACOVAZZO, G ;
GUAGLIARDI, A ;
BURLA, MC ;
POLIDORI, G ;
CAMALLI, M .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1994, 27 :435-435
[2]   2'-DEOXY-2'-METHYLENECYTIDINE AND 2'-DEOXY-2',2'-DIFLUOROCYTIDINE 5'-DIPHOSPHATES - POTENT MECHANISM-BASED INHIBITORS OF RIBONUCLEOTIDE REDUCTASE [J].
BAKER, CH ;
BANZON, J ;
BOLLINGER, JM ;
STUBBE, J ;
SAMANO, V ;
ROBINS, MJ ;
LIPPERT, B ;
JARVI, E ;
RESVICK, R .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (06) :1879-1884
[3]   SYNTHESIS AND X-RAY STRUCTURE OF THE 1ST NONPOLYMERIC CHLOROTETRAKIS(CARBOXYLATO)-DIRUTHENIUM(II,III) COMPOUND [J].
BARRAL, MC ;
JIMENEZAPARICIO, R ;
ROYER, EC ;
RUIZVALERO, C ;
SAUCEDO, MJ ;
URBANOS, FA .
INORGANIC CHEMISTRY, 1994, 33 (12) :2692-2694
[4]   3'-DEOXY-3'-(VINYLSULPHONYL)THYMIDINE - A NEW REACTIVE ANALOG OF AZT - ITS SYNTHESIS AND REACTIVITIES TOWARDS VARIOUS NUCLEOPHILES [J].
BERA, S ;
SAKTHIVEL, K ;
PATHAK, T ;
LANGLEY, GJ .
TETRAHEDRON, 1995, 51 (28) :7857-7866
[5]   C-NUCLEOSIDE STUDIES .21. SYNTHESIS OF SOME HYDROXYALKYLATED PYRROLO[3,2-D]PYRIMIDINES AND THIENO-[3,2-D]PYRIMIDINES RELATED TO KNOWN ANTIVIRAL ACYCLONUCLEOSIDES [J].
BUCHANAN, JG ;
CRAVEN, DA ;
WIGHTMAN, RH ;
HARNDEN, MR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (01) :195-202
[6]  
CASIRAGHI G, 1992, TETRAHEDRON, V48, P5619
[7]   SYNTHESIS AND CHARACTERIZATION OF PORPHYRIN-SUGAR CARBON CONJUGATES [J].
CASIRAGHI, G ;
CORNIA, M ;
ZANARDI, F ;
RASSU, G ;
RAGG, E ;
BORTOLINI, R .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (07) :1801-1808
[8]  
Casiraghi G., 1992, NAT PROD LETT, V1, P45
[9]  
CASTRO J, 1994, TRANSIT METAL CHEM, V19, P343
[10]   SYNTHESIS AND STRUCTURE OF 1,10-PHENANTHROLINE BIS (2-[(2-PYRROLE)METHYLIMINO]PHENOLATO)COBALT(II) [J].
CASTRO, J ;
ROMERO, J ;
GARCIAVAZQUEZ, JA ;
SOUSA, A ;
CASTINEIRAS, A .
JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 1994, 24 (07) :469-472