tert-butyl (2S,3S)-3-[benzyl-[(1S)-1-phenylethyl]amino]-6-(1,3-dioxoisoindol-2-yl)-2-fluorohexanoate | 1253232-94-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: tert-butyl (2S,3S)-3-[benzyl-[(1S)-1-phenylethyl]amino]-6-(1,3-dioxoisoindol-2-yl)-2-fluorohexanoate
• CAS: 1253232-94-8
• 化学式: C₃₃H₃₇FN₂O₄
• 分子量: 544.666
• InChiKey: KSQAIKDXUHSLAD-OIFPXGRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,3S)-3-[benzyl-[(1S)-1-phenylethyl]amino]-6-(1,3-dioxoisoindol-2-yl)-2-fluorohexanoate 在 水 、 甲胺 作用下， 以 乙醇 为溶剂， 反应 2.5h， 生成
  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
• 作为产物：
  描述：

  邻苯二甲酸亚胺 、 (2S,3S,αS)-tert-butyl 6-hydroxy-3-(N-benzyl-α-methylbenzylamino)-2-fluorohexanoate 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以97%的产率得到tert-butyl (2S,3S)-3-[benzyl-[(1S)-1-phenylethyl]amino]-6-(1,3-dioxoisoindol-2-yl)-2-fluorohexanoate
  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.