Phosphorous acid dimethyl ester 2-trimethylsilanyl-ethyl ester | 750629-17-5

• 英文名称: Phosphorous acid dimethyl ester 2-trimethylsilanyl-ethyl ester
• CAS: 750629-17-5
• 化学式: C₇H₁₉O₃PSi
• 分子量: 210.285
• InChiKey: YMEJXUJMVHMAKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  12.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Phosphorous acid dimethyl ester 2-trimethylsilanyl-ethyl ester 在 硼烷四氢呋喃络合物 、 苯硫酚 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 生成 triethylammonium methyl 2-(trimethylsilyl)ethyl boranophosphate
  参考文献：
  名称：

  A Novel Method for the Synthesis of Dinucleoside Boranophosphates by a Boranophosphotriester Method

  摘要：

  2'-Deoxyribonucleoside-3'-boranophosphates (nucleotide monomers), including four kinds of nucleobases, were synthesized in good yields by the use of new boranophosphorylating reagents. We have explored various kinds of condensing reagents as well as nucleophilic catalysts for the boranophosphorylation reaction with nucleosides. In the synthesis of dinucleoside boranophosphates, undesirable side reactions occurred at the O-4 of thymine and the O-6 of N-2-phenylacetylguanine bases. To avoid these side reactions, additional protecting groups, benzoyl (Bz) and diphenylcarbamoyl (Dpc) groups, were introduced to thymine and guanine bases, respectively. As a result, the condensation reactions proceeded smoothly without any side reactions, and the dimers including four kinds of nucleobases were obtained in excellent yields. In the deprotection of the 5'-DMTr group, Et3SiH was found to be effective as a scavenger for the DMTr cation which caused a P-B bond cleavage. After removal of the other protecting groups by the conventional procedure, four kinds of dinucleoside boranophosphates were obtained in good yields.

  DOI：

  10.1021/jo0493875
• 作为产物：
  描述：

  甲醇 、 2-(trimethylsilyl)ethyl dichlorophosphite 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 以77%的产率得到Phosphorous acid dimethyl ester 2-trimethylsilanyl-ethyl ester
  参考文献：
  名称：

  A Novel Method for the Synthesis of Dinucleoside Boranophosphates by a Boranophosphotriester Method

  摘要：

  2'-Deoxyribonucleoside-3'-boranophosphates (nucleotide monomers), including four kinds of nucleobases, were synthesized in good yields by the use of new boranophosphorylating reagents. We have explored various kinds of condensing reagents as well as nucleophilic catalysts for the boranophosphorylation reaction with nucleosides. In the synthesis of dinucleoside boranophosphates, undesirable side reactions occurred at the O-4 of thymine and the O-6 of N-2-phenylacetylguanine bases. To avoid these side reactions, additional protecting groups, benzoyl (Bz) and diphenylcarbamoyl (Dpc) groups, were introduced to thymine and guanine bases, respectively. As a result, the condensation reactions proceeded smoothly without any side reactions, and the dimers including four kinds of nucleobases were obtained in excellent yields. In the deprotection of the 5'-DMTr group, Et3SiH was found to be effective as a scavenger for the DMTr cation which caused a P-B bond cleavage. After removal of the other protecting groups by the conventional procedure, four kinds of dinucleoside boranophosphates were obtained in good yields.

  DOI：

  10.1021/jo0493875