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核酸成分类似物:由5-取代-4-羟基-6(1H)-嘧啶酮合成2'-脱氧核苷

Nucleic acid component analogues: synthesis of 2'-deoxynucleosides from 5-substituted-4-hydroxy-6(1H)-pyrimidinones.

作者信息

Khattab Ahmed F, Abdel Megied Ahmed E S, Pedersen Erik B

机构信息

Chemistry Department, Faculty of Science, Monoufiya University, Shebien El-Koam, A. R. Egypt.

出版信息

Nucleosides Nucleotides Nucleic Acids. 2003;22(1):99-107. doi: 10.1081/NCN-120018626.

DOI:10.1081/NCN-120018626
PMID:12708804
Abstract

Condensation of the silylated pyrimidines 5a-c with methyl 2-deoxy-3,5-di-O-toluoyl-D-pentofuranoside 6, using trimethylsilyltriflate as catalyst gave anomeric mixtures of 2'-deoxynucleosides 7a-c, the pure alpha- and beta-anomers were separated and deprotected with sodium methoxide in methanol to give 1-(2'-deoxy-alpha-D-pentafuranosyl)-4-hydroxy-5-substituted-6(1H)-pyrimidinones 10a,b and 13a and their corresponding beta-anomers 11a,b and 13b.

摘要

使用三氟甲磺酸三甲基硅酯作为催化剂,使硅烷化嘧啶5a - c与2 - 脱氧 - 3,5 - 二 - O - 甲苯甲酰基 - D - 戊呋喃糖苷6缩合,得到2'-脱氧核苷7a - c的异头物混合物,将纯的α - 和β - 异头物分离,并用甲醇中的甲醇钠脱保护,得到1 - (2'-脱氧 - α - D - 戊呋喃糖基)-4 - 羟基 - 5 - 取代 - 6(1H)-嘧啶酮10a、b和13a及其相应的β - 异头物11a、b和13b。

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