5'-O-(4,4'-dimethoxytrityl)-3'-O-(triethylsilyl)-3'-C-(1,1-dimethylpropanoyl)thymidine | 220928-55-2

• 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: 5'-O-(4,4'-dimethoxytrityl)-3'-O-(triethylsilyl)-3'-C-(1,1-dimethylpropanoyl)thymidine
• 英文别名: 1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-(2,2-dimethylpropanoyl)-4-triethylsilyloxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 220928-55-2
• 化学式: C₄₂H₅₄N₂O₈Si
• 分子量: 742.985
• InChiKey: CTVLIPZMKFIHLZ-WOBWMNBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.53
• 重原子数：
  53
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5'-O-(4,4'-dimethoxytrityl)-3'-O-(triethylsilyl)-3'-C-(1,1-dimethylpropanoyl)thymidine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以84%的产率得到5'-O-(4,4'-dimethoxytrityl)-3'-C-(2,2-dimethylpropanoyl)thymidine
  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-(4,4'-dimethoxytrityl)-3'-C-(hydroxymethyl)thymidine 在 吡啶 、 咪唑 、 N-甲基吲哚酮 、 cerium(III) chloride 、 四丙基高钌酸铵 、 4 Angstroems MS 、 氢氟酸 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 37.0h， 生成 5'-O-(4,4'-dimethoxytrityl)-3'-O-(triethylsilyl)-3'-C-(1,1-dimethylpropanoyl)thymidine
  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.