(2S,3R)-2-(4-tert-Butoxy-benzyl)-3-(diethoxy-phosphoryl)-aziridine-1-carboxylic acid tert-butyl ester | 471880-27-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2S,3R)-2-(4-tert-Butoxy-benzyl)-3-(diethoxy-phosphoryl)-aziridine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2R,3S)-2-diethoxyphosphoryl-3-[[4-[(2-methylpropan-2-yl)oxy]phenyl]methyl]aziridine-1-carboxylate
• CAS: 471880-27-0
• 化学式: C₂₂H₃₆NO₆P
• 分子量: 441.505
• InChiKey: OPGXVCWUVLWJCD-HXIJRHRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  74.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2-(4-tert-Butoxy-benzyl)-3-(diethoxy-phosphoryl)-aziridine-1-carboxylic acid tert-butyl ester 在 palladium on activated charcoal 氢气 作用下， 生成 [(R)-1-tert-Butoxycarbonylamino-3-(4-tert-butoxy-phenyl)-propyl]-phosphonic acid diethyl ester
  参考文献：
  名称：

  An efficient synthesis of α- and β-aminophosphonic esters from α-amino acids

  摘要：

  Catalytic hydrogenation of N-Boc aziridine 2-phosphonates derived from 3-amino-2-hydroxyphosphonates affords N-Boc alpha-aminophosphonic esters in high enantiomeric purities. Alternatively, the alpha-hydroxy beta-aminophosphonic esters can be reduced into beta-aminophosphonic esters by radical deoxygenation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01035-3
• 作为产物：
  描述：

  Boc-D-Tyr(tBu)-H 在 potassium fluoride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 (2S,3R)-2-(4-tert-Butoxy-benzyl)-3-(diethoxy-phosphoryl)-aziridine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  An efficient synthesis of α- and β-aminophosphonic esters from α-amino acids

  摘要：

  Catalytic hydrogenation of N-Boc aziridine 2-phosphonates derived from 3-amino-2-hydroxyphosphonates affords N-Boc alpha-aminophosphonic esters in high enantiomeric purities. Alternatively, the alpha-hydroxy beta-aminophosphonic esters can be reduced into beta-aminophosphonic esters by radical deoxygenation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01035-3

文献信息

• An efficient synthesis of α- and β-aminophosphonic esters from α-amino acids
  作者：Cyrille Pousset、Marc Larchevêque

  DOI：10.1016/s0040-4039(02)01035-3

  日期：2002.7

  Catalytic hydrogenation of N-Boc aziridine 2-phosphonates derived from 3-amino-2-hydroxyphosphonates affords N-Boc alpha-aminophosphonic esters in high enantiomeric purities. Alternatively, the alpha-hydroxy beta-aminophosphonic esters can be reduced into beta-aminophosphonic esters by radical deoxygenation. (C) 2002 Elsevier Science Ltd. All rights reserved.