1-(3-C-benzoyl-2-deoxy-β-D-threo-pentofuranosyl)thymine | 220928-51-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-(3-C-benzoyl-2-deoxy-β-D-threo-pentofuranosyl)thymine
• 英文别名: 1-[(2R,4R,5R)-4-benzoyl-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 220928-51-8
• 化学式: C₁₇H₁₈N₂O₆
• 分子量: 346.34
• InChiKey: JRVMNSGNPZUWBR-PBFPGSCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  116
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,4'-双甲氧基三苯甲基氯 、 1-(3-C-benzoyl-2-deoxy-β-D-threo-pentofuranosyl)thymine 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 反应 15.0h， 以81%的产率得到1-(5-O-(4,4'-dimethoxytrityl)-3-C-benzoyl-2-deoxy-β-D-threo-pentofuranosyl)thymine
  参考文献：
  名称：

  C-3‘-Branched Thymidines as Precursors for the Selective Generation of C-3‘-Nucleoside Radicals

  摘要：

  C-3'-nucleoside radicals can be generated via Norrish type I photocleavage of C-3'-acyl nucleoside derivatives. In monomer experiments employing C-3'-acylthymidine derivatives 2 and 3, a 1:1 mixture of isomers of the H-abstraction products was obtained when the photolysis was carried out in the presence of a hydrogen donor. Derivatives 2 were synthesized by an approach which involves the formation of a silyl-protected cyanohydrin, which is subsequently alkylated with organolithium reagents, followed by hydrolysis. Derivatives 3 could be obtained via a multistep synthesis starting from diol 7. Several different methods were attempted to oxidize the unprotected diol to the alpha-hydroxy aldehyde. Finally, a route was chosen which involves a protection-deprotection sequence followed by oxidation of the free primary alcohol. The resulting modified nucleosides should facilitate the study of C-3'-DNA radicals.

  DOI：

  10.1021/jo982022y
• 作为产物：
  描述：

  5'-(O-tert-butyl(dimethyl)silyl)-3'-ketothymidine 在 盐酸 、 copper(l) iodide 、 18-冠醚-6 作用下， 以 二氯甲烷 为溶剂， 反应 46.0h， 生成 1-(3-C-benzoyl-2-deoxy-β-D-threo-pentofuranosyl)thymine
  参考文献：
  名称：

  C-3‘-Branched Thymidines as Precursors for the Selective Generation of C-3‘-Nucleoside Radicals

  摘要：

  C-3'-nucleoside radicals can be generated via Norrish type I photocleavage of C-3'-acyl nucleoside derivatives. In monomer experiments employing C-3'-acylthymidine derivatives 2 and 3, a 1:1 mixture of isomers of the H-abstraction products was obtained when the photolysis was carried out in the presence of a hydrogen donor. Derivatives 2 were synthesized by an approach which involves the formation of a silyl-protected cyanohydrin, which is subsequently alkylated with organolithium reagents, followed by hydrolysis. Derivatives 3 could be obtained via a multistep synthesis starting from diol 7. Several different methods were attempted to oxidize the unprotected diol to the alpha-hydroxy aldehyde. Finally, a route was chosen which involves a protection-deprotection sequence followed by oxidation of the free primary alcohol. The resulting modified nucleosides should facilitate the study of C-3'-DNA radicals.

  DOI：

  10.1021/jo982022y

文献信息

• C-3‘-Branched Thymidines as Precursors for the Selective Generation of C-3‘-Nucleoside Radicals
  作者：Steffi Körner、Amanda Bryant-Friedrich、Bernd Giese

  DOI：10.1021/jo982022y

  日期：1999.3.1

  C-3'-nucleoside radicals can be generated via Norrish type I photocleavage of C-3'-acyl nucleoside derivatives. In monomer experiments employing C-3'-acylthymidine derivatives 2 and 3, a 1:1 mixture of isomers of the H-abstraction products was obtained when the photolysis was carried out in the presence of a hydrogen donor. Derivatives 2 were synthesized by an approach which involves the formation of a silyl-protected cyanohydrin, which is subsequently alkylated with organolithium reagents, followed by hydrolysis. Derivatives 3 could be obtained via a multistep synthesis starting from diol 7. Several different methods were attempted to oxidize the unprotected diol to the alpha-hydroxy aldehyde. Finally, a route was chosen which involves a protection-deprotection sequence followed by oxidation of the free primary alcohol. The resulting modified nucleosides should facilitate the study of C-3'-DNA radicals.