diethyl (S)-2-hydroxy-3-(triphenylmethylamino)propylphosphonate | 643014-29-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: diethyl (S)-2-hydroxy-3-(triphenylmethylamino)propylphosphonate
• 英文别名: (2S)-1-diethoxyphosphoryl-3-(tritylamino)propan-2-ol
• CAS: 643014-29-3
• 化学式: C₂₆H₃₂NO₄P
• 分子量: 453.518
• InChiKey: WTTZUTHATFLCGD-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl (S)-2-hydroxy-3-(triphenylmethylamino)propylphosphonate 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 (S)-Methoxy-phenyl-acetic acid (S)-1-(tert-butoxycarbonylamino-methyl)-2-(diethoxy-phosphoryl)-ethyl ester
  参考文献：
  名称：

  An efficient synthesis of an enantiomerically pure phosphonate analogue of l-GABOB

  摘要：

  Two reliable methods for the synthesis of the enantiomerically pure (S)-3-amino-2-hydroxypropylphosphonic acid (a phosphonate analogue Of L-GABOB) from diethyl (S)-2,3-epoxypropylphosphonate are elaborated. The amplification of the enantiomeric purity of the intermediate diethyl (S)-3-(tert-butoxycarbonylamino)- and (S)-3-(diphenylmethylamino)-2-hydroxy-propylphosphonates was observed on a silica get column. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.09.006
• 作为产物：
  描述：

  三苯甲胺 、 (S)-(-)-diethyl 2,3-epoxypropylphosphonate 以 甲苯 为溶剂， 反应 168.0h， 以76%的产率得到diethyl (S)-2-hydroxy-3-(triphenylmethylamino)propylphosphonate
  参考文献：
  名称：

  An efficient synthesis of an enantiomerically pure phosphonate analogue of l-GABOB

  摘要：

  Two reliable methods for the synthesis of the enantiomerically pure (S)-3-amino-2-hydroxypropylphosphonic acid (a phosphonate analogue Of L-GABOB) from diethyl (S)-2,3-epoxypropylphosphonate are elaborated. The amplification of the enantiomeric purity of the intermediate diethyl (S)-3-(tert-butoxycarbonylamino)- and (S)-3-(diphenylmethylamino)-2-hydroxy-propylphosphonates was observed on a silica get column. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.09.006

文献信息

• An efficient synthesis of an enantiomerically pure phosphonate analogue of l-GABOB
  作者：Andrzej E. Wróblewski、Anetta Hałajewska-Wosik

  DOI：10.1016/j.tetasy.2003.09.006

  日期：2003.10

  Two reliable methods for the synthesis of the enantiomerically pure (S)-3-amino-2-hydroxypropylphosphonic acid (a phosphonate analogue Of L-GABOB) from diethyl (S)-2,3-epoxypropylphosphonate are elaborated. The amplification of the enantiomeric purity of the intermediate diethyl (S)-3-(tert-butoxycarbonylamino)- and (S)-3-(diphenylmethylamino)-2-hydroxy-propylphosphonates was observed on a silica get column. (C) 2003 Elsevier Ltd. All rights reserved.