1-(5-O-(4,4'-dimethoxytrityl)-3-C-acetyl-2-deoxy-β-D-threo-pentofuranosyl)thymine | 220928-41-6

• 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-acetyl-2-deoxy-β-D-threo-pentofuranosyl)thymine
• 英文别名: 1-[(2R,4R,5R)-4-acetyl-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 220928-41-6
• 化学式: C₃₃H₃₄N₂O₈
• 分子量: 586.642
• InChiKey: AKYAJYOQGKOXTF-PUCLRWMGSA-N

物化性质

• 密度：
  1.282±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  1-(5-O-(4,4'-dimethoxytrityl)-3-C-acetyl-2-deoxy-β-D-threo-pentofuranosyl)thymine 在 t-butyltin 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 1-(2'-deoxy-5'-O-4,4'-dimethoxytrityl-β-D-threo-pentofuranosyl)-thymine 、 保护胸苷
  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 、 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 49.0h， 生成 1-(5-O-(4,4'-dimethoxytrityl)-3-C-acetyl-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

• Generation of a C-3‘-Thymidinyl Radical in Single-Stranded Oligonucleotides under Anaerobic Conditions
  作者：Amanda C. Bryant-Friedrich

  DOI：10.1021/ol0493453

  日期：2004.7.1

  [reaction: see text] A C-3'-thymidinyl radical has been photochemically generated site-specifically in DNA oligonucleotides. A nucleoside H-phosphonate bearing a C-3' acetyl group was incorporated into DNA oligomers using a hand-coupling technique. When nucleotides containing the modified monomer were photolyzed (> or =320 nm) in the presence of a hydrogen atom donor, reduction products were detected

  [反应：见正文]在DNA寡核苷酸中已位点特异性地化学生成了C-3'-嘧啶基。使用手工偶联技术将带有C-3'乙酰基的核苷H-膦酸酯掺入DNA低聚物中。当在氢原子供体的存在下将含有修饰单体的核苷酸进行光解（>或= 320 nm）时，通过RP-HPLC和MALDI-ToF MS分析检测到还原产物。