4-oxo-pentanoic acid 5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-[{5-(6-benzoylamino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yloxy}-(2-cyano-ethoxy)-thiophosphoryloxymethyl]-tetrahydro-furan-3-yl ester | 262429-99-2

• 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-oxo-pentanoic acid 5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-[{5-(6-benzoylamino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yloxy}-(2-cyano-ethoxy)-thiophosphoryloxymethyl]-tetrahydro-furan-3-yl ester
• CAS: 262429-99-2
• 化学式: C₆₂H₆₀N₉O₁₄PS
• 分子量: 1218.25
• InChiKey: BXIHUGGPYRLMAH-GOESGWSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.03
• 重原子数：
  87.0
• 可旋转键数：
  26.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  277.69
• 氢给体数：
  2.0
• 氢受体数：
  22.0

反应信息

• 作为反应物：
  描述：

  4-oxo-pentanoic acid 5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-[{5-(6-benzoylamino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yloxy}-(2-cyano-ethoxy)-thiophosphoryloxymethyl]-tetrahydro-furan-3-yl ester 在 一水合肼 作用下， 以 溶剂黄146 为溶剂， 反应 0.17h， 生成 N-[1-[(2R,4S,5R)-5-[[[(2R,3S,5R)-5-(6-benzamidopurin-9-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]oxolan-3-yl]oxy-(2-cyanoethoxy)phosphinothioyl]oxymethyl]-4-hydroxyoxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide
  参考文献：
  名称：

  Investigation of a Facile Synthetic Method for Phosphorothioate Dimer Synthons In Oligonucleotide Phosphorothioates Synthesis

  摘要：

  A facile synthetic method of a phosphorothioate dimer block was investigated. Dinucleoside phosphite triester intermediates were obtained in one-pot synthesis by the coupling of a protected nucleoside bearing free 5'-OH and a protected nucleoside bearing free 3'-OH in the presence of phosphorous trichloride (PCl3) and 1,2,4-triazole. The intermediates were easily sulfurized to afford the desired phosphorothioate dimer blocks in 33-64% overall yields.

  DOI：

  10.1080/15257770008033035
• 作为产物：
  描述：

  N-benzoyl-3'-O-levulinoyl-2'-deoxy-β-D-cytidine 在 N-甲基吗啉 、 1H-1,2,4-三唑 、 sulfur 、 三氯化磷 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 3.5h， 生成 4-oxo-pentanoic acid 5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-[{5-(6-benzoylamino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yloxy}-(2-cyano-ethoxy)-thiophosphoryloxymethyl]-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Investigation of a Facile Synthetic Method for Phosphorothioate Dimer Synthons In Oligonucleotide Phosphorothioates Synthesis

  摘要：

  A facile synthetic method of a phosphorothioate dimer block was investigated. Dinucleoside phosphite triester intermediates were obtained in one-pot synthesis by the coupling of a protected nucleoside bearing free 5'-OH and a protected nucleoside bearing free 3'-OH in the presence of phosphorous trichloride (PCl3) and 1,2,4-triazole. The intermediates were easily sulfurized to afford the desired phosphorothioate dimer blocks in 33-64% overall yields.

  DOI：

  10.1080/15257770008033035

文献信息

• Synthesis of Dimer Phosphoramidite Synthons for Oligodeoxyribonucleotide Phosphorothioates Using Diethyldithiocarbonate disulfide as an Efficient Sulfurizing Reagent
  作者：Alessandra Eleuteri、Zacharia S. Cheruvallath、Daniel C. Capaldi、Douglas L. Cole Vasulinga、T. Ravikumar

  DOI：10.1080/07328319908044844

  日期：1999.8

  An efficient solution phase synthesis of deoxyribonucleoside phosphorothioate dimers utilizing phosphoramidite approach is described. Diethyldithiocarbonate disulfide (DDD) was found to be an efficient sulfurizing reagent in the conversion of phosphite triesters to phosphorothioate triesters.