(S)-ethyl 2-[[(S)-(2,6-diisopropylphenoxy)(methoxymethyl)phosphoryl]amino]propanoate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-ethyl 2-[[(S)-(2,6-diisopropylphenoxy)(methoxymethyl)phosphoryl]amino]propanoate
• 英文别名: ethyl (2S)-2-[[[2,6-di(propan-2-yl)phenoxy]-(methoxymethyl)phosphoryl]amino]propanoate
• 化学式: C₁₉H₃₂NO₅P
• 分子量: 385.441
• InChiKey: VBZDDQROOJHQGF-HAWMADMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  ethyl (2S)-2-[[benzyloxymethyl-(2,6-diisopropylphenoxy)phosphoryl]amino]propanoate 在 palladium 10% on activated carbon 、 氢气 、 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 (S)-ethyl 2-[[(S)-(2,6-diisopropylphenoxy)(methoxymethyl)phosphoryl]amino]propanoate
  参考文献：
  名称：

  Oral Delivery of Propofol with Methoxymethylphosphonic Acid as the Delivery Vehicle

  摘要：

  Phosphonamidate 3a of methoxymethylphosphonic acid (MMPA) with propofol (l) and L-alanine ethyl ester was found to be an efficient scaffold for the oral delivery of compound 1. The synthesis and evaluation of MMPA based phosphonamidates of compound 1, HSK3486 (2), and other phenolic drugs revealed the general application of MMPA as the effective delivery vehicle for phenolic drugs. On the basis of plasma concentrations of compound 1 and SN38 (14), the oral bioavailability of compound 3a and 15 in beagle dogs was found to be 97.6% and 34.1%, respectively.

  DOI：

  10.1021/acs.jmedchem.7b01133