2'-O-[1-(4-chlorophenyl)-4-ethoxypiperidin-4-yl]-5'-O-(4,4-dimethoxytrityl)uridine | 908141-00-4

• 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: 2'-O-[1-(4-chlorophenyl)-4-ethoxypiperidin-4-yl]-5'-O-(4,4-dimethoxytrityl)uridine
• CAS: 908141-00-4
• 化学式: C₄₃H₄₆ClN₃O₉
• 分子量: 784.306
• InChiKey: DNRUHTYRGMTONJ-BAYOHDFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.89
• 重原子数：
  56.0
• 可旋转键数：
  14.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  133.71
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2'-O-[1-(4-chlorophenyl)-4-ethoxypiperidin-4-yl]-5'-O-(4,4-dimethoxytrityl)uridine 、 双(二异丙基氨基)(2-氰基乙氧基)膦 以 乙腈 为溶剂， 生成 3-[[(2R,3R,4R,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[1-(4-chlorophenyl)-4-ethoxypiperidin-4-yl]oxy-5-(2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
  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-{(2R,3R,3aR,9aR)-3-[1-(4-Chloro-phenyl)-4-ethoxy-piperidin-4-yloxy]-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl}-1H-pyrimidine-2,4-dione 在 吡啶 、 四乙基氟化铵水合物 作用下， 以 四氢呋喃 为溶剂， 生成 2'-O-[1-(4-chlorophenyl)-4-ethoxypiperidin-4-yl]-5'-O-(4,4-dimethoxytrityl)uridine
  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

文献信息

• Synthesis and characterization of mannosylated oligoribonucleotides
  作者：Yuyan Zhao、Kha Tram、Hongbin Yan

  DOI：10.1016/j.carres.2009.08.033

  日期：2009.11

  Oligoribonucleotide (RNA)-carbohydrate conjugates bearing mono- and divalent mannosides were readily obtained using 3,4-diethoxy-3-cyclobutene-1,2-dione as the linking agent in the presence of trace amount of triethylamine. The glycoconjugates were purified by HPLC and characterized by electrospray mass spectroscopy.

  在痕量三乙胺的存在下，使用3,4-二乙氧基-3-环丁烯-1,2-二酮作为连接剂，可以轻松获得带有一价和二价甘露糖苷的寡核糖核苷酸（RNA）-碳水化合物共轭物。糖缀合物通过HPLC纯化，并通过电喷雾质谱法表征。