(5R)-5-[(2-methylpropan-2-yl)oxy]-5-[oxido-di(propan-2-yloxy)phosphaniumyl]pent-1-ene | 634582-98-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: (5R)-5-[(2-methylpropan-2-yl)oxy]-5-[oxido-di(propan-2-yloxy)phosphaniumyl]pent-1-ene
• CAS: 634582-98-2
• 化学式: C₁₅H₃₁O₄P
• 分子量: 306.382
• InChiKey: QUWODVRGONRJRC-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5R)-5-[(2-methylpropan-2-yl)oxy]-5-[oxido-di(propan-2-yloxy)phosphaniumyl]pent-1-ene 在 碘 作用下， 以 乙腈 为溶剂， 以41%的产率得到(2S,5S)-2-(iodomethyl)-5-[oxido-di(propan-2-yloxy)phosphaniumyl]oxolane
  参考文献：
  名称：

  A stereoselective route to bioactive nucleotide phosphonate analogs

  摘要：

  Recently we have reported a novel class of tetrahydrofuran phosplionates of which trans guanine nucleotide analog la showed potent antiviral activity as well as antitumor activity. In this paper we describe a stereoselective route where the key step involves an iodoetherification of a alpha-hydroxyphosphonate to generate the trans tetrahydrofuran with high stereoselectivity. The same intermediate 2 was also used to access the key intermediate for the cis analog 1b. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.071
• 作为产物：
  描述：

  三异丙基亚磷酸酯 在 三氟化硼乙醚 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 环己烷 、 甲苯 为溶剂， 反应 5.0h， 生成 (5R)-5-[(2-methylpropan-2-yl)oxy]-5-[oxido-di(propan-2-yloxy)phosphaniumyl]pent-1-ene
  参考文献：
  名称：

  A stereoselective route to bioactive nucleotide phosphonate analogs

  摘要：

  Recently we have reported a novel class of tetrahydrofuran phosplionates of which trans guanine nucleotide analog la showed potent antiviral activity as well as antitumor activity. In this paper we describe a stereoselective route where the key step involves an iodoetherification of a alpha-hydroxyphosphonate to generate the trans tetrahydrofuran with high stereoselectivity. The same intermediate 2 was also used to access the key intermediate for the cis analog 1b. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.071

文献信息

• A stereoselective route to bioactive nucleotide phosphonate analogs
  作者：Monica Bubenik、Patrice Préville、Josée Dugas、Giorgio Attardo、Laval Chan

  DOI：10.1016/j.tetlet.2003.09.071

  日期：2003.11

  Recently we have reported a novel class of tetrahydrofuran phosplionates of which trans guanine nucleotide analog la showed potent antiviral activity as well as antitumor activity. In this paper we describe a stereoselective route where the key step involves an iodoetherification of a alpha-hydroxyphosphonate to generate the trans tetrahydrofuran with high stereoselectivity. The same intermediate 2 was also used to access the key intermediate for the cis analog 1b. (C) 2003 Elsevier Ltd. All rights reserved.