1'-苯基硒核苷的合成及自由基反应。

Nucleic acids symposium series Pub Date : 2000-01-01 DOI:10.1093/nass/44.1.109

T Kodama, M Nomura, S Shuto, A Matsuda

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引用次数: 0

摘要

通过在3'，5'-O-TIPDS-2'-酮吡啶(1)的1'-位置烯醇化，成功合成了1'- -苯基硒尿嘧啶衍生物(4)。在4的2'-羟基上引入乙烯基硅醚作为分子内自由基受体后，其原子转移自由基环化反应，然后用TBAF处理得到1'- -乙烯基尿嘧啶衍生物(10)。用该方法成功合成了1′α -乙烯尿嘧啶(11)和-胞苷(14)。

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Synthesis and radical reaction of 1'-phenylselenonucleosides.

The 1'alpha-phenylselenouridine derivative (4) was successfully synthesized via enolization at the 1'-position of the 3',5'-O-TIPDS-2'-ketouridine (1). After the introduction of a vinylsilyl tether as an intramolecular radical acceptor at the 2'-hydroxy group of 4, its atom-transfer radical cyclization reaction, followed by the treatment with TBAF gave 1'alpha-vinyluridine derivative (10). Using this procedure, 1'alpha-vinyluridine (11) and -cytidine (14) were successfully synthesized.

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Nucleic acids symposium series

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