(2S,3S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-2-fluoro-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid | 1253233-00-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (2S,3S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-2-fluoro-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid
• CAS: 1253233-00-9
• 化学式: C₂₆H₃₁FN₂O₆
• 分子量: 486.54
• InChiKey: OPPQDLLOJDLJOV-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  二碳酸二叔丁酯 、 在 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 以34 mg的产率得到(2S,3S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-2-fluoro-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid
  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