(+)-(1α,3α,5β)-3-acetoxy-5-(diethylphosphonomethoxy)cyclopentanol | 161085-55-8

• 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: (+)-(1α,3α,5β)-3-acetoxy-5-(diethylphosphonomethoxy)cyclopentanol
• 英文别名: (1R,3S,4S)-1-Acetoxy-4-(diethylphosphono)methoxycyclopentan-3-ol；[(1R,3S,4S)-3-(diethoxyphosphorylmethoxy)-4-hydroxycyclopentyl] acetate
• CAS: 161085-55-8
• 化学式: C₁₂H₂₃O₇P
• 分子量: 310.284
• InChiKey: AOZHEHIZOBAGCA-WOPDTQHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (+)-(1α,3α,5β)-3-acetoxy-5-(diethylphosphonomethoxy)cyclopentanol 在 potassium cyanide 作用下， 以 甲醇 为溶剂， 生成 (+/-)-(1α,3α,4β)-4-(diethylphosphonomethoxy)cyclopentane-1,3-diol 、 (+)-(1α,3α,4β)-4-(diethylphosphonomethoxy)cyclopentane-1,3-diol
  参考文献：
  名称：

  Synthesis of the phosphonate isostere of carbocyclic 5-bromovinyldeoxyuridine monophosphate

  摘要：

  The nucleotide analogue 5 has been synthesized, via formation of the diet 11, and has been shown to be inactive against HSV in vitro. Resolution of the intermediate diol 11 was effected using a highly stereoselective enzyme-catalysed acetylation.

  DOI：

  10.1039/p19940003061
• 作为产物：
  描述：

  1,4/2-cyclopentanetriol 在 2,6-二甲基吡啶 、 正丁基锂 、 Lipase PS Amano 、 氢氟酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 36.33h， 生成 (+)-(1α,3α,5β)-3-acetoxy-5-(diethylphosphonomethoxy)cyclopentanol
  参考文献：
  名称：

  Synthesis of the phosphonate isostere of carbocyclic 5-bromovinyldeoxyuridine monophosphate

  摘要：

  The nucleotide analogue 5 has been synthesized, via formation of the diet 11, and has been shown to be inactive against HSV in vitro. Resolution of the intermediate diol 11 was effected using a highly stereoselective enzyme-catalysed acetylation.

  DOI：

  10.1039/p19940003061

文献信息

• Drake, Alex F.; Garofalo, Antonio; Hillman, Jennifer M. L., Journal of the Chemical Society. Perkin transactions I, 1996, # 22, p. 2739 - 2746
  作者：Drake, Alex F.、Garofalo, Antonio、Hillman, Jennifer M. L.、Merlo, Valeria、McCague, Ray、Roberts, Stanley M.

  DOI：——

  日期：——
• Synthesis of the phosphonate isostere of carbocyclic 5-bromovinyldeoxyuridine monophosphate
  作者：Diane M. Coe、Antonio Garofalo、Stanley M. Roberts、Richard Storer、Andrew J. Thorpe

  DOI：10.1039/p19940003061

  日期：——

  The nucleotide analogue 5 has been synthesized, via formation of the diet 11, and has been shown to be inactive against HSV in vitro. Resolution of the intermediate diol 11 was effected using a highly stereoselective enzyme-catalysed acetylation.