Synthesis of N-(trimethylsilylethoxycarbonyl)-deoxycytidine and deoxy-adenosine derivatives as key intermediates for the DNA synthesis using fluoride ion-promoted deprotection strategy

被引:5
作者
Sekine, M [1 ]
Tobe, M [1 ]
Nagayama, T [1 ]
Wada, T [1 ]
机构
[1] Tokyo Inst Technol, Japan Sci & Technol Agcy, JST, CREST, Yokohama, Kanagawa 2268501, Japan
关键词
Teoc group; base-sensitive; N-protected nucleosides; DNA/RNA chemical synthesis; protecting group;
D O I
10.2174/1570178043488419
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An improved method for the synthesis of trimethylsilylethyl chloroformate (Teoc-Cl) was studied in great detail. N-Teoc-adenosine. X-Teoc-cytidine and their deoxyribonucleoside derivatives were synthesized as the key synthetic intermediates for the synthesis of base-sensitive oligonucleotide derivatives by use of N-methylimidazole. The stability and chemical properties of these N-protected nucleoside derivatives were examined.
引用
收藏
页码:179 / 182
页数:4
相关论文
共 15 条
[1]   SOLID-PHASE SYNTHESIS OF H-PHE-TYR-(PATAT)-NH2 - A NUCLEOPEPTIDE FRAGMENT FROM THE NUCLEOPROTEIN OF BACTERIOPHAGE-PHI-X174 [J].
DREEFTROMP, CM ;
VANDAM, EMA ;
VANDENELST, H ;
VANDERMAREL, GA ;
VANBOOM, JH .
NUCLEIC ACIDS RESEARCH, 1990, 18 (22) :6491-6495
[2]  
ECKERT H, 1987, ANGEW CHEM, V99, P922
[3]   ALLYLOXYCARBONYL GROUP - A VERSATILE BLOCKING GROUP FOR NUCLEOTIDE SYNTHESIS [J].
HAYAKAWA, Y ;
KATO, H ;
UCHIYAMA, M ;
KAJINO, H ;
NOYORI, R .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (12) :2400-2402
[4]   THE PARA-NITROPHENYLETHYL (NPE) GROUP - A VERSATILE NEW BLOCKING GROUP FOR PHOSPHATE AND AGLYCONE PROTECTION IN NUCLEOSIDES AND NUCLEOTIDES [J].
HIMMELSBACH, F ;
SCHULZ, BS ;
TRICHTINGER, T ;
CHARUBALA, R ;
PFLEIDERER, W .
TETRAHEDRON, 1984, 40 (01) :59-72
[5]   2-DIPHENYLMETHYLSILYLETHYL GROUP AS A NEW PROTECTING GROUP OF INTERNUCLEOTIDIC PHOSPHATES IN OLIGONUCLEOTIDE SYNTHESIS [J].
HONDA, S ;
HATA, T .
TETRAHEDRON LETTERS, 1981, 22 (22) :2093-2096
[6]  
HONDA S, 1979, NUCL AC S SER, V6, pS185
[7]  
IYER RP, 2000, CURRENT PROTOCOLS NU, V1
[8]  
KOZYUKOV VP, 1968, ZH OBSHCHEIE KHIM, V38, P1179
[9]   Synthesis of antisense oligonucleotides with minimum depurination [J].
Krotz, AH ;
Cole, DL ;
Ravikumar, VT .
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2003, 22 (02) :129-134
[10]   A novel approach to oligodeoxyribonucleotides bearing phosphoric acid esters at the 3′-terminals via the phosphoramidite method with allyl protection:: An efficient synthesis of base-labile nucleotide-amino acid and -peptide conjugates [J].
Sakakura, A ;
Hayakawa, Y ;
Harada, H ;
Hirose, M ;
Noyori, R .
TETRAHEDRON LETTERS, 1999, 40 (23) :4359-4362