5'-O-(4,4'-Dimethoxytrityl)thymidine 3'-monophosphate 3'-(methoxycarbonylmethyl 2-chlorophenyl) ester | 160711-95-5

• 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)thymidine 3'-monophosphate 3'-(methoxycarbonylmethyl 2-chlorophenyl) ester
• CAS: 160711-95-5
• 化学式: C₄₀H₄₀ClN₂O₁₂P
• 分子量: 807.191
• InChiKey: HZGCHOBTPDQNCU-MICLYWDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.57
• 重原子数：
  56.0
• 可旋转键数：
  16.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  162.84
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  5'-O-(4,4'-Dimethoxytrityl)thymidine 3'-monophosphate 3'-(methoxycarbonylmethyl 2-chlorophenyl) ester 在 吡啶 、 ammonium hydroxide 作用下， 生成
  参考文献：
  名称：

  Novel solid supports for the preparation of 3′-derivatized oligonucleotides: Introduction of 3′-alkylphosphate tether groups bearing amino, carboxy, carboxamido, and mercapto functionalities

  摘要：

  Syntheses of 5 non-nucleosidic solid supports (1-5) that enable preparation of oligonucleotides bearing a carboxy,-amino,-carboxamido,-or mercaptoalkyl spacer arm at their 3'-terminus are described. They all contain an ester bond of moderate susceptibility toward nucleophiles. Upon the completion of oligonucleotide chain assembly, this bond may be cleaved by a variety of nucleophiles. These release the oligonucleotide from the support and simultaneously introduce the desired functionality. Differences in the reactivity between the supports prepared are discussed.

  DOI：

  10.1016/s0040-4020(01)85244-3
• 作为产物：
  描述：

  羟乙酸甲酯 、 保护胸苷 、 2-氯苯基二氯膦 在 1H-1,2,3-三氮唑 、 三乙胺 作用下， 生成 5'-O-(4,4'-Dimethoxytrityl)thymidine 3'-monophosphate 3'-(methoxycarbonylmethyl 2-chlorophenyl) ester
  参考文献：
  名称：

  Novel solid supports for the preparation of 3′-derivatized oligonucleotides: Introduction of 3′-alkylphosphate tether groups bearing amino, carboxy, carboxamido, and mercapto functionalities

  摘要：

  Syntheses of 5 non-nucleosidic solid supports (1-5) that enable preparation of oligonucleotides bearing a carboxy,-amino,-carboxamido,-or mercaptoalkyl spacer arm at their 3'-terminus are described. They all contain an ester bond of moderate susceptibility toward nucleophiles. Upon the completion of oligonucleotide chain assembly, this bond may be cleaved by a variety of nucleophiles. These release the oligonucleotide from the support and simultaneously introduce the desired functionality. Differences in the reactivity between the supports prepared are discussed.

  DOI：

  10.1016/s0040-4020(01)85244-3

文献信息

• Imidazole Tethered Oligodeoxyribonucleotides: Synthesis and RNA Cleaving Activity
  作者：Jari Hovinen、Andrei Guzaev、Elena Azhayeva、Alex Azhayev、Harri Lonnberg

  DOI：10.1021/jo00112a047

  日期：1995.4

  A solid support (3) and a non-nucleosidic phosphoramidite building block (4), both containing a thioester bond is their structure, were synthesized. They were used in the preparation of oligonucleotides tethered to an imidazole group at their 3'- or 5'-terminus, as well as at the 1'-position of nonterminal 3'-deoxypsicothymidine units. The desired functional groups were introduced during the deprotection of the oligonucleotide by using the primary amino group of histamine or 1-(3-aminopropyl)imidazole as a nucleophile. The ability of the tethered oligonucleotides to hydrolyze complementary RNA strands was tested. Of the oligonucleotides prepared, 12b, bearing a histamine group at the 3'-end, was shown to promote a sequence specific strand scission of RNA in the presence of Zn2+ ions.