P1-acyclothymidinyl-P1-borano-P2,P3-dioxo-cyclotriphosphite | 577971-42-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: P1-acyclothymidinyl-P1-borano-P2,P3-dioxo-cyclotriphosphite
• 英文别名: P¹-acyclothymidinyl-P¹-borano-P²,P³-dioxo-cyclotriphosphite
• CAS: 577971-42-7
• 化学式: C₈H₁₆BN₂O₁₁P₃
• 分子量: 419.954
• InChiKey: DTTBRMAWDRKKSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.86
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  175.61
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  P1-acyclothymidinyl-P1-borano-P2,P3-dioxo-cyclotriphosphite 在 水 、 三乙胺 作用下， 反应 5.0h， 生成 acyclothymidine (α-P-orano)triphosphate
  参考文献：
  名称：

  Synthesis of Acyclothymidine Triphosphate and α-P-Boranotriphosphate and Their Substrate Properties with Retroviral Reverse Transcriptase

  摘要：

  graphicThe first example of an acyclonucleoside alpha-P-boranotriphosphate has been synthesized via a phosphoramidite approach in a one-pot reaction with good yield. The presence of the alpha-P-BH3 in 5b results in a 9-fold increase in efficiency of incorporation by MMLV retroviral reverse transcriptase relative to non-boronated 5a in pre-steady-state conditions. The preliminary results indicate that acyclonucleoside alpha-P-boranotriphosphates may have promising applications as a probe of enzyme mechanisms and in the design of new antiviral drugs.

  DOI：

  10.1021/ol034538w
• 作为产物：
  描述：

  1-(2-羟基乙氧基)甲基-5-甲基尿嘧啶 在 四氮唑 、 4-二甲氨基吡啶 、 dimethyl sulfide borane 、 (Bu₃NH)2P₂O₇ 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 1.0h， 生成 P1-acyclothymidinyl-P1-borano-P2,P3-dioxo-cyclotriphosphite
  参考文献：
  名称：

  Synthesis of Acyclothymidine Triphosphate and α-P-Boranotriphosphate and Their Substrate Properties with Retroviral Reverse Transcriptase

  摘要：

  graphicThe first example of an acyclonucleoside alpha-P-boranotriphosphate has been synthesized via a phosphoramidite approach in a one-pot reaction with good yield. The presence of the alpha-P-BH3 in 5b results in a 9-fold increase in efficiency of incorporation by MMLV retroviral reverse transcriptase relative to non-boronated 5a in pre-steady-state conditions. The preliminary results indicate that acyclonucleoside alpha-P-boranotriphosphates may have promising applications as a probe of enzyme mechanisms and in the design of new antiviral drugs.

  DOI：

  10.1021/ol034538w