1-(5-O-(4,4'-dimethoxytrityl)-3-C-(1,1-dimethylpropanoyl)-2-deoxy-β-D-threo-pentofuranosyl)thymine | 220928-52-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-(5-O-(4,4'-dimethoxytrityl)-3-C-(1,1-dimethylpropanoyl)-2-deoxy-β-D-threo-pentofuranosyl)thymine
• 英文别名: 1-[(2R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-(2,2-dimethylpropanoyl)-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 220928-52-9
• 化学式: C₃₆H₄₀N₂O₈
• 分子量: 628.722
• InChiKey: PGEWRGXEMPYGGN-WAINPOFTSA-N

物化性质

• 密度：
  1.239±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  46
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  三乙胺 、 1-(5-O-(4,4'-dimethoxytrityl)-3-C-(1,1-dimethylpropanoyl)-2-deoxy-β-D-threo-pentofuranosyl)thymine 在 咪唑 、 三氯化磷 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到
  参考文献：
  名称：

  Automated synthesis, characterization, and structural analysis of oligonucleotide C-3′-radical precursors

  摘要：

  C-3'-Acyl-3'-xylothymidine-containing oligonucleotides have been designed and synthesized for their use as radical precursors in the study of oxidative DNA damage initiated by a C-3'-radical. These oligomers were efficiently obtained using automated DNA synthesis techniques based on H-phosphonate chemistry. CD spectra and melting curves of the synthesized oligonucleotides were compared to those of their unmodified and xylomodified counterparts. The conformational analysis and hybridization studies indicate that the combination of the photolabile acyl group and the inversion of configuration at the sugar has no profound effect oil the overall conformation of C-3'-acyl-2'-deoxy-3'-xylonucleotides as compared to their natural analogues. These systems should provide excellent tools for the elucidation of DNA damage processes. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.11.038
• 作为产物：
  描述：

  5'-(O-tert-butyl(dimethyl)silyl)-3'-ketothymidine 在 盐酸 、 4-二甲氨基吡啶 、 copper(l) iodide 、 18-冠醚-6 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 97.0h， 生成 1-(5-O-(4,4'-dimethoxytrityl)-3-C-(1,1-dimethylpropanoyl)-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

• Automated synthesis, characterization, and structural analysis of oligonucleotide C-3′-radical precursors
  作者：Georges Lahoud、Jesse Fancher、Sanda Grosu、Breyanna Cavanaugh、Amanda Bryant-Friedrich

  DOI：10.1016/j.bmc.2005.11.038

  日期：2006.4

  C-3'-Acyl-3'-xylothymidine-containing oligonucleotides have been designed and synthesized for their use as radical precursors in the study of oxidative DNA damage initiated by a C-3'-radical. These oligomers were efficiently obtained using automated DNA synthesis techniques based on H-phosphonate chemistry. CD spectra and melting curves of the synthesized oligonucleotides were compared to those of their unmodified and xylomodified counterparts. The conformational analysis and hybridization studies indicate that the combination of the photolabile acyl group and the inversion of configuration at the sugar has no profound effect oil the overall conformation of C-3'-acyl-2'-deoxy-3'-xylonucleotides as compared to their natural analogues. These systems should provide excellent tools for the elucidation of DNA damage processes. (c) 2005 Elsevier Ltd. All rights reserved.
• 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.