N-(9-{3-[1-(4-chloro-phenyl)-4-ethoxy-piperidin-4-yloxy]-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl}-6-oxo-6,9-dihydro-1H-purin-2-yl)-2-phenoxy-acetamide | 908140-99-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: N-(9-{3-[1-(4-chloro-phenyl)-4-ethoxy-piperidin-4-yloxy]-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl}-6-oxo-6,9-dihydro-1H-purin-2-yl)-2-phenoxy-acetamide
• CAS: 908140-99-8
• 化学式: C₃₁H₃₅ClN₆O₈
• 分子量: 655.107
• InChiKey: RVKTXOOJDOVCTG-QTWDEJAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.46
• 重原子数：
  46.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  173.29
• 氢给体数：
  4.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  N-(9-{3-[1-(4-chloro-phenyl)-4-ethoxy-piperidin-4-yloxy]-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl}-6-oxo-6,9-dihydro-1H-purin-2-yl)-2-phenoxy-acetamide 在 吡啶 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  LARGE-SCALE SYNTHESIS OF “Cpep” RNA MONOMERS AND THEIR APPLICATION IN AUTOMATED RNA SYNTHESIS

  摘要：

  Small interfering RNAs (siRNA) are the latest candidates for oligonucleotide-based therapeutics. Should siRNA be successful in clinical trials, a huge demand for synthetic RNA is anticipated. We believe that 1-(4-chlorophenyl)-4-ethoxypiperidin-4-yl(Cpep) is an ideal 2'-protecting group for large-scale syntheses. Unlike 2'-silyl groups, mild acid hydrolysis instead of fluoride ion is used for the 2'-deprotection. The syntheses of 2'-Cpep protected nucleosides (A, Q G, and U) has been accomplished on a 0.5 Kg scale. The 2'-Cpep monomers were transformed into 3'-O-phosphoramidites for conventional automated solid-phase synthesis. Cost-effective processes for large-scale synthesis of Cpep monomers and initial automated solid-phase synthesis are demonstrated.

  DOI：

  10.1081/ncn-200060150
• 作为产物：
  描述：

  1-(4-Chlorophenyl)-4-ethoxy-1,2,5,6-tetrahydropyridine 在 二氯乙酸 、 四乙基氟化铵水合物 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 N-(9-{3-[1-(4-chloro-phenyl)-4-ethoxy-piperidin-4-yloxy]-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl}-6-oxo-6,9-dihydro-1H-purin-2-yl)-2-phenoxy-acetamide
  参考文献：
  名称：

  LARGE-SCALE SYNTHESIS OF “Cpep” RNA MONOMERS AND THEIR APPLICATION IN AUTOMATED RNA SYNTHESIS

  摘要：

  Small interfering RNAs (siRNA) are the latest candidates for oligonucleotide-based therapeutics. Should siRNA be successful in clinical trials, a huge demand for synthetic RNA is anticipated. We believe that 1-(4-chlorophenyl)-4-ethoxypiperidin-4-yl(Cpep) is an ideal 2'-protecting group for large-scale syntheses. Unlike 2'-silyl groups, mild acid hydrolysis instead of fluoride ion is used for the 2'-deprotection. The syntheses of 2'-Cpep protected nucleosides (A, Q G, and U) has been accomplished on a 0.5 Kg scale. The 2'-Cpep monomers were transformed into 3'-O-phosphoramidites for conventional automated solid-phase synthesis. Cost-effective processes for large-scale synthesis of Cpep monomers and initial automated solid-phase synthesis are demonstrated.

  DOI：

  10.1081/ncn-200060150