dimethyl (1R,2S)-(2-tert-butoxycarbonyloamino-1-hydroxy-4-methyl)pentylphosphonate

• 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: dimethyl (1R,2S)-(2-tert-butoxycarbonyloamino-1-hydroxy-4-methyl)pentylphosphonate
• 英文别名: tert-butyl N-[(1R,2S)-1-[dimethoxy(oxido)phosphaniumyl]-1-hydroxy-4-methylpentan-2-yl]carbamate
• 化学式: C₁₃H₂₈NO₆P
• 分子量: 325.342
• InChiKey: CUBGYRYOSBNLAX-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  100
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-叔丁氧羰基-L-亮氨醇 在 potassium fluoride 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.25h， 生成 dimethyl (1R,2S)-(2-tert-butoxycarbonyloamino-1-hydroxy-4-methyl)pentylphosphonate
  参考文献：
  名称：

  Stereoselective synthesis, solution structure and metal complexes of (1S,2S)-2-amino-1-hydroxyalkylphosphonic acids

  摘要：

  The highly stereoselective synthesis of (1S,2S)-2-amino-1-hydroxyalkylphosphonic acids was achieved by addition of dimethyl phosphite to N-protected aminoaldehydes. Relative configuration and solution conformations of (1S,2S)-2-amino-lhydroxy-alkylphosphonic acids (in D2O) and their dimethyl esters (in CDCl3 and CD3OD) were established by means of NMR basing on the dependence between observed values of coupling constants ((3)J(HH), (3)J(PC), (3)J(HP)) and corresponding dihedral angles. Potentiometric and spectroscopic methods were used for the evaluation of the structure of the complexes of (1S,2S)-2-amino-lhydroxy-alkylphosphonic acids with Zn(II) and Cu(II) ions in aqueous solutions. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00278-7

文献信息

• Stereoselective synthesis, solution structure and metal complexes of (1S,2S)-2-amino-1-hydroxyalkylphosphonic acids
  作者：Marcin Drag、Rafal Latajka、Elzbieta Gumienna-Kontecka、Henryk Kozlowski、Pawel Kafarski

  DOI：10.1016/s0957-4166(03)00278-7

  日期：2003.7

  The highly stereoselective synthesis of (1S,2S)-2-amino-1-hydroxyalkylphosphonic acids was achieved by addition of dimethyl phosphite to N-protected aminoaldehydes. Relative configuration and solution conformations of (1S,2S)-2-amino-lhydroxy-alkylphosphonic acids (in D2O) and their dimethyl esters (in CDCl3 and CD3OD) were established by means of NMR basing on the dependence between observed values of coupling constants ((3)J(HH), (3)J(PC), (3)J(HP)) and corresponding dihedral angles. Potentiometric and spectroscopic methods were used for the evaluation of the structure of the complexes of (1S,2S)-2-amino-lhydroxy-alkylphosphonic acids with Zn(II) and Cu(II) ions in aqueous solutions. (C) 2003 Elsevier Science Ltd. All rights reserved.