4'α-C-(2-aminoethyl)-3'-O-(tert-butyldimethylsilyl)-5'-O-(dimethoxytrityl)thymidine | 310889-52-2

• 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: 4'α-C-(2-aminoethyl)-3'-O-(tert-butyldimethylsilyl)-5'-O-(dimethoxytrityl)thymidine
• 英文别名: 1-[(2R,4S,5R)-5-(2-aminoethyl)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[tert-butyl(dimethyl)silyl]oxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 310889-52-2
• 化学式: C₃₉H₅₁N₃O₇Si
• 分子量: 701.935
• InChiKey: IHWFVXAJRDHKLA-ZVRNNNLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.27
• 重原子数：
  50.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  127.03
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  4'α-C-(2-aminoethyl)-3'-O-(tert-butyldimethylsilyl)-5'-O-(dimethoxytrityl)thymidine 在 4-二甲氨基吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 为溶剂， 反应 96.5h， 生成 5'-O-(dimethoxytrityl)-4'-C-[N-(cholesteryloxycarbonyl)aminoethyl]-3'-O-(succinyl)thymidine
  参考文献：
  名称：

  Nucleosides and Nucleotides. Part 206: Introduction of Lipophilic Groups into 4′α-C-(2-Aminoethyl)thymidine-Containing Phosphodiester Oligodeoxynucleotides and Thermal Stabilities of the Duplexes

  摘要：

  Synthesis and properties of the 4'alpha-C-(2-aminoethyl)thymidine (1)-containing oligodeoxynucleotides (ODNs), which have lipophilic groups such as palmitic acid, oleic acid, and cholesterol at the terminal of the aminoethyl linker of the compound 1, are described. The ODNs were synthesized in a DNA synthesizer by using controlled pore glasses (CPGs) having the 4'alpha-C-[N-(palmitoyl), N-(oleoyl), and N-(cholesteryloxycarbonyl)aminoethyl]thymidine analogs (9a, b, and c). The stability of the duplexes formed by these ODNs and a complementary DNA 15 or RNA 16 was studied by thermal denaturation. It was found that the bulky functional group such as cholesterol thermally destabilizes the DNA/DNA duplexes, but that such thermal destabilization can be offset by the effects of the aminoethyl linker of 1. Furthermore, these lipophilic groups do not largely influence the thermal stability of the DNA/RNA duplexes. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00705-5
• 作为产物：
  描述：

  4'α-C-(2-azidoethyl)-3'-O-(tert-butyldimethylsilyl)-5'-O-(dimethoxytrityl)thymidine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 24.0h， 以95%的产率得到4'α-C-(2-aminoethyl)-3'-O-(tert-butyldimethylsilyl)-5'-O-(dimethoxytrityl)thymidine
  参考文献：
  名称：

  Nucleosides and Nucleotides. Part 206: Introduction of Lipophilic Groups into 4′α-C-(2-Aminoethyl)thymidine-Containing Phosphodiester Oligodeoxynucleotides and Thermal Stabilities of the Duplexes

  摘要：

  Synthesis and properties of the 4'alpha-C-(2-aminoethyl)thymidine (1)-containing oligodeoxynucleotides (ODNs), which have lipophilic groups such as palmitic acid, oleic acid, and cholesterol at the terminal of the aminoethyl linker of the compound 1, are described. The ODNs were synthesized in a DNA synthesizer by using controlled pore glasses (CPGs) having the 4'alpha-C-[N-(palmitoyl), N-(oleoyl), and N-(cholesteryloxycarbonyl)aminoethyl]thymidine analogs (9a, b, and c). The stability of the duplexes formed by these ODNs and a complementary DNA 15 or RNA 16 was studied by thermal denaturation. It was found that the bulky functional group such as cholesterol thermally destabilizes the DNA/DNA duplexes, but that such thermal destabilization can be offset by the effects of the aminoethyl linker of 1. Furthermore, these lipophilic groups do not largely influence the thermal stability of the DNA/RNA duplexes. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00705-5