Synthesis of 4'-C-acylated thymidines

被引:62
作者
Marx, A [1 ]
Erdmann, P [1 ]
Senn, M [1 ]
Korner, S [1 ]
Jungo, T [1 ]
Petretta, M [1 ]
Imwinkelried, P [1 ]
Dussy, A [1 ]
Kulicke, KJ [1 ]
Macko, L [1 ]
Zehnder, M [1 ]
Giese, B [1 ]
机构
[1] UNIV BASEL,DEPT CHEM,CH-4056 BASEL,SWITZERLAND
关键词
D O I
10.1002/hlca.19960790720
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Two synthetic pathways towards 4'-C-acylthymidines are presented. These modified mononucleosides are precursors of the 2'-deoxyribonucleotide 4'-C-radical. They were converted into their corresponding 3'-O-[(2-cyanoethyl) N,N-diisopropylphosphoramidites] 3a-c and incorporated in oligonucleotides by solid-phase synthesis. The structure of some modified nucleosides was revealed by X-ray crystal-structure analysis.
引用
收藏
页码:1980 / 1994
页数:15
相关论文
共 29 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]   CONFORMATIONAL-ANALYSIS OF SUGAR RING IN NUCLEOSIDES AND NUCLEOTIDES - IMPROVED METHOD FOR INTERPRETATION OF PROTON MAGNETIC-RESONANCE COUPLING-CONSTANTS [J].
ALTONA, C ;
SUNDARALINGAM, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (07) :2333-2344
[3]   (1'-C-13)-2'-DEOXYRIBONUCLEOSIDES - STRUCTURAL AND CONFORMATIONAL INSIGHTS DERIVED FROM C-13-H-1 SPIN COUPLING-CONSTANTS INVOLVING C1' [J].
BANDYOPADHYAY, T ;
WU, J ;
SERIANNI, AS .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (20) :5513-5517
[4]   A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287
[5]  
DESS DB, 1983, J ORG CHEM, V48, P4156
[6]  
GIESE B, 1994, SYNTHESIS-STUTTGART, P1310
[7]   CLEAVAGE OF SINGLE-STRANDED 4'-OLIGONUCLEOTIDE RADICALS IN THE PRESENCE OF O2 [J].
GIESE, B ;
BEYRICHGRAF, X ;
ERDMANN, P ;
GIRAUD, L ;
IMWINKELRIED, P ;
MULLER, SN ;
SCHWITTER, U .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (22) :6146-6147
[8]  
GIESE B, 1994, SYNLETT, P1003
[9]   MECHANISM OF NEOCARZINOSTATIN ACTION - ROLE OF DNA MICROSTRUCTURE IN DETERMINATION OF CHEMISTRY OF BISTRANDED OXIDATIVE DAMAGE [J].
GOLDBERG, IH .
ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (07) :191-198
[10]   ACYCLIC STEREOSELECTION .7. STEREOSELECTIVE SYNTHESIS OF 2-ALKYL-3-HYDROXY CARBONYL-COMPOUNDS BY ALDOL CONDENSATION [J].
HEATHCOCK, CH ;
BUSE, CT ;
KLESCHICK, WA ;
PIRRUNG, MC ;
SOHN, JE ;
LAMPE, J .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (06) :1066-1081