tert-butyl (3S)-3-[benzyl-[(1S)-1-phenylethyl]amino]-6-[bis[(2-methylpropan-2-yl)oxycarbonyl]amino]hexanoate | 1253233-04-3

• 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: tert-butyl (3S)-3-[benzyl-[(1S)-1-phenylethyl]amino]-6-[bis[(2-methylpropan-2-yl)oxycarbonyl]amino]hexanoate
• CAS: 1253233-04-3
• 化学式: C₃₅H₅₂N₂O₆
• 分子量: 596.808
• InChiKey: AZEXKOPBSHZZKL-WNJJXGMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  43
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  85.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  tert-butyl (E)-6-(N,N-di-tert-butoxycarbonylamino)hex-2-enoate 、 (S)-(-)-N-苄基-1-苯基-乙胺 在 正丁基锂 、 氯化铵 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 2.0h， 以44%的产率得到tert-butyl (3S)-3-[benzyl-[(1S)-1-phenylethyl]amino]-6-[bis[(2-methylpropan-2-yl)oxycarbonyl]amino]hexanoate
  参考文献：
  名称：

  Enantioselective Synthesis of α-Fluoro-β³-amino Esters: Synthesis of Enantiopure, Orthogonally Protected α-Fluoro-β³-lysine

  摘要：

  The scope of a tandem conjugate addition fluorination sequence performed on alpha,beta-unsaturated esters using the enantiopure lithium amide derived from (S)-N-benzyl-N-(alpha-methylbenzyl)amine, and the electrophilic fluorinating agent N-fluorobenzenesulfonimide has been investigated. Using this method, a-fluoro-beta(3)-amino esters can be obtained in up to quantitative yield and 80:20 to >99:1 dr. This simple methodology does not rely on the use of alpha-amino acids from the chiral pool and thus provides the potential for the preparation of enantiopure alpha-fluoro-beta(3)-amino acids with a wide variety of side chains. Its utility was demonstrated through the synthesis of orthogonally protected (2S,3S)-alpha-fluoro-beta(3)-lysine.

  DOI：

  10.1021/jo101600c

文献信息

• Enantioselective Synthesis of α-Fluoro-β³-amino Esters: Synthesis of Enantiopure, Orthogonally Protected α-Fluoro-β³-lysine
  作者：Peter J. Duggan、Martin Johnston、Taryn L. March

  DOI：10.1021/jo101600c

  日期：2010.11.5

  The scope of a tandem conjugate addition fluorination sequence performed on alpha,beta-unsaturated esters using the enantiopure lithium amide derived from (S)-N-benzyl-N-(alpha-methylbenzyl)amine, and the electrophilic fluorinating agent N-fluorobenzenesulfonimide has been investigated. Using this method, a-fluoro-beta(3)-amino esters can be obtained in up to quantitative yield and 80:20 to >99:1 dr. This simple methodology does not rely on the use of alpha-amino acids from the chiral pool and thus provides the potential for the preparation of enantiopure alpha-fluoro-beta(3)-amino acids with a wide variety of side chains. Its utility was demonstrated through the synthesis of orthogonally protected (2S,3S)-alpha-fluoro-beta(3)-lysine.