(1S,2S)-2-(dibenzylamino)-1-[diethoxy(oxido)phosphaniumyl]-2-phenylethanol | 421551-20-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2S)-2-(dibenzylamino)-1-[diethoxy(oxido)phosphaniumyl]-2-phenylethanol
• CAS: 421551-20-4
• 化学式: C₂₆H₃₂NO₄P
• 分子量: 453.518
• InChiKey: NBLUOYARMBDPKM-UIOOFZCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 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：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 (1S,2S)-2-(dibenzylamino)-1-[diethoxy(oxido)phosphaniumyl]-2-phenylethanol 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 以89%的产率得到diethyl (1S,2S)-2-[(tert-butoxycarbonyl)amino]-1-hydroxy-2-phenylethyl-phosphonate
  参考文献：
  名称：

  Stereochemistry of the addition of dialkyl phosphites to (S)-N,N-dibenzylphenylglycinal

  摘要：

  The addition of various dialkyl phosphite derivatives to (S)-N,N-dibenzylphenylglycinal 6 led to the preponderance of anti over syn diastereoisomers: from 75:25 when NEt3 or Ti(OiPr)(4) were used to 51:49 for Li or Mg salts. In the NEt3-catalysed reaction, partially racemised phosphonates were formed, while enantiomeric products were obtained after addition of lithium O,O-dimethylphosphonate to (S)-6 at -70degreesC. Because the syn-isomers were found to be resistant to O-benzoylation, Mixtures of diastereoisomers were easily separated after esterification of the anti products. Hydrogenation of the syn-phosphonates in the presence of Boc(2)O gave enantiomeric dialkyl N-Boc-2-amino-1-hydroxy-2-phenylethylphosphonates-phosphonate analogues of the docetaxel C-13 side chain. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00526-2
• 作为产物：
  描述：

  (S)-2-(N,N-dibenzylamino)-2-phenylethanol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (1S,2S)-2-(dibenzylamino)-1-[diethoxy(oxido)phosphaniumyl]-2-phenylethanol
  参考文献：
  名称：

  Stereochemistry of the addition of dialkyl phosphites to (S)-N,N-dibenzylphenylglycinal

  摘要：

  The addition of various dialkyl phosphite derivatives to (S)-N,N-dibenzylphenylglycinal 6 led to the preponderance of anti over syn diastereoisomers: from 75:25 when NEt3 or Ti(OiPr)(4) were used to 51:49 for Li or Mg salts. In the NEt3-catalysed reaction, partially racemised phosphonates were formed, while enantiomeric products were obtained after addition of lithium O,O-dimethylphosphonate to (S)-6 at -70degreesC. Because the syn-isomers were found to be resistant to O-benzoylation, Mixtures of diastereoisomers were easily separated after esterification of the anti products. Hydrogenation of the syn-phosphonates in the presence of Boc(2)O gave enantiomeric dialkyl N-Boc-2-amino-1-hydroxy-2-phenylethylphosphonates-phosphonate analogues of the docetaxel C-13 side chain. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00526-2

文献信息

• Stereochemistry of the addition of dialkyl phosphites to (S)-N,N-dibenzylphenylglycinal
  作者：Andrzej E. Wróblewski、Dorota G. Piotrowska

  DOI：10.1016/s0957-4166(01)00526-2

  日期：2001.11

  The addition of various dialkyl phosphite derivatives to (S)-N,N-dibenzylphenylglycinal 6 led to the preponderance of anti over syn diastereoisomers: from 75:25 when NEt3 or Ti(OiPr)(4) were used to 51:49 for Li or Mg salts. In the NEt3-catalysed reaction, partially racemised phosphonates were formed, while enantiomeric products were obtained after addition of lithium O,O-dimethylphosphonate to (S)-6 at -70degreesC. Because the syn-isomers were found to be resistant to O-benzoylation, Mixtures of diastereoisomers were easily separated after esterification of the anti products. Hydrogenation of the syn-phosphonates in the presence of Boc(2)O gave enantiomeric dialkyl N-Boc-2-amino-1-hydroxy-2-phenylethylphosphonates-phosphonate analogues of the docetaxel C-13 side chain. (C) 2002 Elsevier Science Ltd. All rights reserved.