[(2R,3S,5R)-5-(4-benzamido-2-oxopyrimidin-1-yl)-2-[[[(2R,3S,5R)-5-(6-benzamidopurin-9-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]oxolan-3-yl]oxy-(2-cyanoethoxy)phosphanyl]oxymethyl]oxolan-3-yl] 4-oxopentanoate | 262430-01-3

• 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: [(2R,3S,5R)-5-(4-benzamido-2-oxopyrimidin-1-yl)-2-[[[(2R,3S,5R)-5-(6-benzamidopurin-9-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]oxolan-3-yl]oxy-(2-cyanoethoxy)phosphanyl]oxymethyl]oxolan-3-yl] 4-oxopentanoate
• CAS: 262430-01-3
• 化学式: C₆₂H₆₀N₉O₁₄P
• 分子量: 1186.18
• InChiKey: QFAFNBJUFOSVHS-GOESGWSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  86
• 可旋转键数：
  27
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  276
• 氢给体数：
  2
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5R)-5-(4-benzamido-2-oxopyrimidin-1-yl)-2-[[[(2R,3S,5R)-5-(6-benzamidopurin-9-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]oxolan-3-yl]oxy-(2-cyanoethoxy)phosphanyl]oxymethyl]oxolan-3-yl] 4-oxopentanoate 在 sulfur 作用下， 以 吡啶 为溶剂， 反应 0.5h， 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
• 作为产物：
  描述：

  N-benzoyl-3'-O-levulinoyl-2'-deoxy-β-D-cytidine 、 N6-苯甲酰基-5'-O-(4,4'-二甲氧基三苯基)-2'-脱氧腺苷 、 3-羟基丙腈 在 N-甲基吗啉 、 1H-1,2,4-三唑 、 三氯化磷 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 [(2R,3S,5R)-5-(4-benzamido-2-oxopyrimidin-1-yl)-2-[[[(2R,3S,5R)-5-(6-benzamidopurin-9-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]oxolan-3-yl]oxy-(2-cyanoethoxy)phosphanyl]oxymethyl]oxolan-3-yl] 4-oxopentanoate
  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

• Investigation of a Facile Synthetic Method for Phosphorothioate Dimer Synthons In Oligonucleotide Phosphorothioates Synthesis
  作者：Takanori Miyashita、Kohei Yamada、Kazuhiko Kondo、Kenya Mori、Kazuo Shinozuka

  DOI：10.1080/15257770008033035

  日期：2000.5

  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.