[(2R)-2-(diethoxyphosphorylmethyl)-3-hydroxypropyl] acetate | 182691-03-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: [(2R)-2-(diethoxyphosphorylmethyl)-3-hydroxypropyl] acetate
• CAS: 182691-03-8
• 化学式: C₁₀H₂₁O₆P
• 分子量: 268.247
• InChiKey: FDQISJMGEHZOCV-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(2R)-2-(diethoxyphosphorylmethyl)-3-hydroxypropyl] acetate 在 jones reagent 作用下， 以 丙酮 为溶剂， 反应 6.0h， 以65%的产率得到(2R)-2-acetoxymethyl-3-diethylphosphonopropionic acid
  参考文献：
  名称：

  Lipase-catalyzed enantioselective acylation of prochiral 2-(ω-phosphono)alkyl-1,3-propanediols: Application to the enantioselective synthesis of ω-phosphono-α-amino acids

  摘要：

  Lipase PS catalyzed acetylation of prochiral 2-(omega-phosphono)alkyl-1,3-propanediols 1a-c was found to proceed with high enantioselectivity. The applications of phosphonic chirons 2a-c thus obtained were illustrated by the stereocontrolled synthesis of omega-phosphono-alpha-amino acids such as L-AP-3, L-AP-4, and N-Boc-L-F(2)Pab(OEt)(2)-OH. Copyright (C) 1996 Published by Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00354-0
• 作为产物：
  描述：

  (2,2-dimethyl-[1,3]dioxan-5-yl methyl)-phosphonic acid diethyl ester 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.5h， 生成 [(2R)-2-(diethoxyphosphorylmethyl)-3-hydroxypropyl] acetate
  参考文献：
  名称：

  Lipase-catalyzed enantioselective acylation of prochiral 2-(ω-phosphono)alkyl-1,3-propanediols: Application to the enantioselective synthesis of ω-phosphono-α-amino acids

  摘要：

  Lipase PS catalyzed acetylation of prochiral 2-(omega-phosphono)alkyl-1,3-propanediols 1a-c was found to proceed with high enantioselectivity. The applications of phosphonic chirons 2a-c thus obtained were illustrated by the stereocontrolled synthesis of omega-phosphono-alpha-amino acids such as L-AP-3, L-AP-4, and N-Boc-L-F(2)Pab(OEt)(2)-OH. Copyright (C) 1996 Published by Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00354-0