5'-O-(4,4'-dimethoxytrityl)-2-N-(2,2'-bis(2-nitrophenyl)ethyloxycarbonyl)-2'-deoxyguanosine 3'-O-(S-pivaloyl-2-thioethyl) N,N-diisopropylphosphoramidite | 243657-27-4

• 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)-2-N-(2,2'-bis(2-nitrophenyl)ethyloxycarbonyl)-2'-deoxyguanosine 3'-O-(S-pivaloyl-2-thioethyl) N,N-diisopropylphosphoramidite
• 英文别名: S-[2-[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-[2-[2,2-bis(2-nitrophenyl)ethoxycarbonylamino]-6-oxo-1H-purin-9-yl]oxolan-3-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxyethyl] 2,2-dimethylpropanethioate
• CAS: 243657-27-4
• 化学式: C₅₉H₆₇N₈O₁₄PS
• 分子量: 1175.27
• InChiKey: LWLGQRKRNFVLSF-KJQNLKICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  83
• 可旋转键数：
  26
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  290
• 氢给体数：
  2
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  S-[2-[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxyethyl] 2,2-dimethylpropanethioate 、 5'-O-(4,4'-dimethoxytrityl)-2-N-(2,2'-bis(2-nitrophenyl)ethyloxycarbonyl)-2'-deoxyguanosine 3'-O-(S-pivaloyl-2-thioethyl) N,N-diisopropylphosphoramidite 生成 S-[2-[[(2R,3S,5R)-2-[[[(2R,3S,5R)-2-[[[(2R,3S,5R)-2-[[[(2R,3S,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-2-[[2-(2,2-dimethylpropanoylsulfanyl)ethoxy-[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyphosphoryl]oxymethyl]oxolan-3-yl]oxy-[2-(2,2-dimethylpropanoylsulfanyl)ethoxy]phosphoryl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-[2-(2,2-dimethylpropanoylsulfanyl)ethoxy]phosphoryl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-[2-(2,2-dimethylpropanoylsulfanyl)ethoxy]phosphoryl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-hydroxyphosphoryl]oxyethyl] 2,2-dimethylpropanethioate
  参考文献：
  名称：

  Photocleavable Protecting Groups as Nucleobase Protections Allowed the Solid-Phase Synthesis of Base-Sensitive SATE-Prooligonucleotides

  摘要：

  The first synthesis of oligodeoxynucleotide heteropolymers carrying base-sensitive S-pivaloylthioethyl (t-Bu-SATE) phosphotriester linkages has been performed. It is based on the use of 6-nitroveratryloxycarbonyl (NVOC) and 2,2'-bis(2-nitrophenyl)ethoxycarbonyl (diNPEOC) groups as nucleobase protections in combination with photolysis deprotection. The synthesis was realized using the phosphoramidite approach on solid support bearing a 1-(o-nitrophenyl)-1,3-propanediol linker. The removal of the protecting groups and the cleavage of the oligonucleotides from the solid support were accomplished in a single photolysis procedure upon UV irradiation at wavelengths >300 nn. Faster deprotection rates were observed for diNPEOC-protected nucleosides and oligomers than with NVOC-protected ones. The synthesis of pentanucleoside t-Bu-SATE-phosphotriesters d((5')TpCpCpCpTp(3')), d((5')TpApApApAp(3')), and d((5')TpGpGpGpTp(3')) and of dodecanucleoside t-Bu-SATE-phosphotriesters and -phosphorothioate d((5')ApCpApCpCpCpApApTpTpCpTp(3')) and d((5')ApGpApApTpTpGpGpGpTpGpTp(3')) demonstrated the efficiency of the method.

  DOI：

  10.1021/jo990479h
• 作为产物：
  描述：

  3',5'-bis-O-trimethylsilyl-2'-deoxyguanosine 在 吡啶 、 二异丙基铵盐四氮唑 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 5'-O-(4,4'-dimethoxytrityl)-2-N-(2,2'-bis(2-nitrophenyl)ethyloxycarbonyl)-2'-deoxyguanosine 3'-O-(S-pivaloyl-2-thioethyl) N,N-diisopropylphosphoramidite
  参考文献：
  名称：

  Photocleavable Protecting Groups as Nucleobase Protections Allowed the Solid-Phase Synthesis of Base-Sensitive SATE-Prooligonucleotides

  摘要：

  The first synthesis of oligodeoxynucleotide heteropolymers carrying base-sensitive S-pivaloylthioethyl (t-Bu-SATE) phosphotriester linkages has been performed. It is based on the use of 6-nitroveratryloxycarbonyl (NVOC) and 2,2'-bis(2-nitrophenyl)ethoxycarbonyl (diNPEOC) groups as nucleobase protections in combination with photolysis deprotection. The synthesis was realized using the phosphoramidite approach on solid support bearing a 1-(o-nitrophenyl)-1,3-propanediol linker. The removal of the protecting groups and the cleavage of the oligonucleotides from the solid support were accomplished in a single photolysis procedure upon UV irradiation at wavelengths >300 nn. Faster deprotection rates were observed for diNPEOC-protected nucleosides and oligomers than with NVOC-protected ones. The synthesis of pentanucleoside t-Bu-SATE-phosphotriesters d((5')TpCpCpCpTp(3')), d((5')TpApApApAp(3')), and d((5')TpGpGpGpTp(3')) and of dodecanucleoside t-Bu-SATE-phosphotriesters and -phosphorothioate d((5')ApCpApCpCpCpApApTpTpCpTp(3')) and d((5')ApGpApApTpTpGpGpGpTpGpTp(3')) demonstrated the efficiency of the method.

  DOI：

  10.1021/jo990479h

文献信息

• Photocleavable Protecting Groups as Nucleobase Protections Allowed the Solid-Phase Synthesis of Base-Sensitive SATE-Prooligonucleotides
  作者：Karine Alvarez、Jean-Jacques Vasseur、Thierry Beltran、Jean-Louis Imbach

  DOI：10.1021/jo990479h

  日期：1999.8.1

  The first synthesis of oligodeoxynucleotide heteropolymers carrying base-sensitive S-pivaloylthioethyl (t-Bu-SATE) phosphotriester linkages has been performed. It is based on the use of 6-nitroveratryloxycarbonyl (NVOC) and 2,2'-bis(2-nitrophenyl)ethoxycarbonyl (diNPEOC) groups as nucleobase protections in combination with photolysis deprotection. The synthesis was realized using the phosphoramidite approach on solid support bearing a 1-(o-nitrophenyl)-1,3-propanediol linker. The removal of the protecting groups and the cleavage of the oligonucleotides from the solid support were accomplished in a single photolysis procedure upon UV irradiation at wavelengths >300 nn. Faster deprotection rates were observed for diNPEOC-protected nucleosides and oligomers than with NVOC-protected ones. The synthesis of pentanucleoside t-Bu-SATE-phosphotriesters d((5')TpCpCpCpTp(3')), d((5')TpApApApAp(3')), and d((5')TpGpGpGpTp(3')) and of dodecanucleoside t-Bu-SATE-phosphotriesters and -phosphorothioate d((5')ApCpApCpCpCpApApTpTpCpTp(3')) and d((5')ApGpApApTpTpGpGpGpTpGpTp(3')) demonstrated the efficiency of the method.