RAPID AND EFFICIENT STEREOCONTROLLED SYNTHESIS OF C-3'-ETHYNYL RIBO AND XYLONUCLEOSIDES BY ORGANOCERIUM ADDITIONS TO 3'-KETONUCLEOSIDES

被引:34
作者
JUNG, PMJ [1 ]
BURGER, A [1 ]
BIELLMANN, JF [1 ]
机构
[1] UNIV STRASBOURG 1,FAC CHIM,CNRS,CHIM ORGAN BIOL LAB,F-67008 STRASBOURG,FRANCE
关键词
D O I
10.1016/0040-4039(94)02434-D
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In order to prepare new anti-retroviral nucleoside analogues, the effect of the group at C-5' on the addition of lithium and cerium trimethylsilylacetylide on 3'-ketonucleosidcs (R(1) = H, R(1) = TBDMS) derived from adenosine and uridine was studied. The best results in respect of yield (56 to 81%) and diastereoselectivity (95:5 to >98:2) were obtained with a cerium reagent (RCcCl(2)).
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页码:1031 / 1034
页数:4
相关论文
共 26 条
[1]   IMPROVED ANTI-TUMOR EFFECTS IN 3'-BRANCHED HOMOLOGS OF 2'-DEOXYTHIOGUANOSINE - SYNTHESIS AND EVALUATION OF THIOGUANINE NUCLEOSIDES OF 2,3-DIDEOXY-3-(HYDROXYMETHYL)-D-ERYTHRO-PENTOFURANOSE [J].
ACTON, EM ;
GOERNER, RN ;
UH, HS ;
RYAN, KJ ;
HENRY, DW ;
CASS, CE ;
LEPAGE, GA .
JOURNAL OF MEDICINAL CHEMISTRY, 1979, 22 (05) :518-525
[2]   ORGANOCERIUM ADDITIONS TO 2'-DEOXY-3'-KETONUCLEOSIDES [J].
BENDER, SL ;
MOFFETT, KK .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (06) :1646-1647
[3]   STRUCTURE DETERMINATION OF A TETRASACCHARIDE - TRANSIENT NUCLEAR OVERHAUSER EFFECTS IN THE ROTATING FRAME [J].
BOTHNERBY, AA ;
STEPHENS, RL ;
LEE, JM ;
WARREN, CD ;
JEANLOZ, RW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (03) :811-813
[4]   NUCLEOSIDES FROM FLUORINATED BRANCHED-CHAIN SUGARS - SOME REACTIONS OF 3-DEOXY-3-FLUORO-3-C-HYDROXYMETHYL-1,2=5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE [J].
BRINK, AJ ;
DEVILLIERS, OG ;
JORDAAN, A .
CARBOHYDRATE RESEARCH, 1977, 54 (02) :285-291
[5]  
CHIDGEAVADZE ZG, 1990, BIOORG KHIM, V16, P678
[6]   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-&
[7]   SYNTHESIS OF 2'-KETOADENOSINES AND 3'-KETOADENOSINES [J].
CREWS, RP ;
BAKER, DC .
NUCLEOSIDES & NUCLEOTIDES, 1983, 2 (03) :275-289
[8]   ORGANOCERIUM ADDITIONS TO HYDRAZONES - EFFECTS OF REAGENT STOICHIOMETRY ON EFFICIENCY AND SELECTIVITY [J].
DENMARK, SE ;
EDWARDS, JP ;
NICAISE, O .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (03) :569-578
[9]  
FEDOROV II, 1990, BIOORG KHIM+, V16, P997
[10]   3'-C-BRANCHED 2'-DEOXY-5-METHYLURIDINES - SYNTHESIS, ENZYME-INHIBITION, AND ANTIVIRAL PROPERTIES [J].
FEDOROV, II ;
KAZMINA, EM ;
NOVICOV, NA ;
GURSKAYA, GV ;
BOCHKAREV, AV ;
JASKO, MV ;
VICTOROVA, LS ;
KUKHANOVA, MK ;
BALZARINI, J ;
DECLERCQ, E ;
KRAYEVSKY, AA .
JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (24) :4567-4575