NUCLEOSIDES AND NUCLEOTIDES .115. SYNTHESIS OF 3-ALKYL-3-DEAZAINOSINES VIA PALLADIUM-CATALYZED INTRAMOLECULAR CYCLIZATION - A NEW CONFORMATIONAL LOCK WITH THE ALKYL GROUP AT THE 3-POSITION OF THE 3-DEAZAINOSINE IN ANTICONFORMATION

被引:11
作者
AOYAGI, M [1 ]
MINAKAWA, N [1 ]
MATSUDA, A [1 ]
机构
[1] HOKKAIDO UNIV,FAC PHARMACEUT SCI,KITA 12,NISHI 6,KITA KU,SAPPORO,HOKKAIDO 060,JAPAN
关键词
PALLADIUM-CATALYZED CYCLIZATION; ALLYL AMINE; NUCLEOSIDE; CONFORMATION; NOE;
D O I
10.1016/S0040-4039(00)60068-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthesis of 3-methyl-3-deazainosine (7a) and 3-ethyl-3-deazainosine (7b) can be done by intramolecular cyclization of 5-iodoimidazole-4-(N-allyl and -crotyl)carboxamide ribosides 4a,b with palladium catalysts. The glycosyl conformer population of 7a,b was analyzed by NOE experiments to be fixed in anti-conformation.
引用
收藏
页码:103 / 106
页数:4
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