P¹-acyclothymidinyl-P²,P³-dioxo-cyclotriphosphite | 577773-71-8

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机含氧阴离子化合物
• 英文名称: P¹-acyclothymidinyl-P²,P³-dioxo-cyclotriphosphite
• 英文别名: 1-[2-[(4,6-Dihydroxy-4,6-dioxo-1,3,5,2,4lambda5,6lambda5-trioxatriphosphinan-2-yl)oxy]ethoxymethyl]-5-methylpyrimidine-2,4-dione；1-[2-[(4,6-dihydroxy-4,6-dioxo-1,3,5,2,4λ5,6λ5-trioxatriphosphinan-2-yl)oxy]ethoxymethyl]-5-methylpyrimidine-2,4-dione
• CAS: 577773-71-8
• 化学式: C₈H₁₃N₂O₁₁P₃
• 分子量: 406.119
• InChiKey: ZCFPHTJAKQTMQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  170
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  P¹-acyclothymidinyl-P²,P³-dioxo-cyclotriphosphite 在 dimethyl sulfide borane 、 水 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 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 、 (Bu₃NH)2P₂O₇ 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 0.5h， 生成 P¹-acyclothymidinyl-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

文献信息

• Synthesis of Acyclothymidine Triphosphate and α-<i>P</i>-Boranotriphosphate and Their Substrate Properties with Retroviral Reverse Transcriptase
  作者：Ping Li、Mikhail Dobrikov、Hongyan Liu、Barbara Ramsay Shaw

  DOI：10.1021/ol034538w

  日期：2003.7.1

  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.