[(2R,3S,5R)-2-[[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-methylphosphanyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] acetate | 129398-92-1

• 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)-2-[[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-methylphosphanyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] acetate
• CAS: 129398-92-1
• 化学式: C₄₄H₄₉N₄O₁₃P
• 分子量: 872.866
• InChiKey: BCRRJEHYRWPZJX-XLHLKVIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.58
• 重原子数：
  62.0
• 可旋转键数：
  16.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  200.63
• 氢给体数：
  2.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5R)-2-[[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-methylphosphanyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] acetate 在 二氯乙酸 、 ammonium hydroxide 、 dimethyl sulfide borane 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 dithymidine P-boranomethylphosphonate
  参考文献：
  名称：

  SYNTHESIS OF A NOVEL NUCLEIC ACID MIMIC: P-BORANOMETHYLPHOSPHONATE

  摘要：

  A new type of non-ionic nucleotide analogue with a doubly modified internucleotide linkage, P-boranomethylphosphonate, has been successfully synthesized and characterized. Dithymidine boranomethylphosphonate 5 is the first example of a P-boranomethylphosphonate compound; it is a highly lipophilic phosphodiester analog, which is almost totally resistant to both snake venom phosphodiesterase (SVPDE) and bovine spleen phosphodiesterase (BSPDE). P-boranomethylphosphonates are expected to be promising candidates for mechanistic, diagnostic and therapeutic applications.

  DOI：

  10.1081/ncn-100002547
• 作为产物：
  描述：

  保护胸苷 在 四氮唑 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 [(2R,3S,5R)-2-[[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-methylphosphanyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] acetate
  参考文献：
  名称：

  SYNTHESIS OF A NOVEL NUCLEIC ACID MIMIC: P-BORANOMETHYLPHOSPHONATE

  摘要：

  A new type of non-ionic nucleotide analogue with a doubly modified internucleotide linkage, P-boranomethylphosphonate, has been successfully synthesized and characterized. Dithymidine boranomethylphosphonate 5 is the first example of a P-boranomethylphosphonate compound; it is a highly lipophilic phosphodiester analog, which is almost totally resistant to both snake venom phosphodiesterase (SVPDE) and bovine spleen phosphodiesterase (BSPDE). P-boranomethylphosphonates are expected to be promising candidates for mechanistic, diagnostic and therapeutic applications.

  DOI：

  10.1081/ncn-100002547

文献信息

• A new DMAP-catalyzed phosphonamidite coupling reaction for synthesis of oligonucleotide methylphosphonate derivatives
  作者：Alexander V. Lebedev、George R. Wenzinger、Eric Wickstrom

  DOI：10.1016/s0040-4039(00)94645-8

  日期：1990.1
• LEBEDEV, ALEXANDER V.;WENZINGER, GEORGE R.;WICKSTROM, ERIC, TETRAHEDRON LETT., 31,(1990) N, C. 851-854
  作者：LEBEDEV, ALEXANDER V.、WENZINGER, GEORGE R.、WICKSTROM, ERIC

  DOI：——

  日期：——