t-butyl (2S,3S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-2-fluoro-3-phenylpropanoate | 698373-56-7

• 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: t-butyl (2S,3S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-2-fluoro-3-phenylpropanoate
• 英文别名: tert-butyl (2S,3S)-3-[benzyl-[(1S)-1-phenylethyl]amino]-2-fluoro-3-phenylpropanoate
• CAS: 698373-56-7
• 化学式: C₂₈H₃₂FNO₂
• 分子量: 433.566
• InChiKey: QOGYNPMFPNGYRH-MZBJOSPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  t-butyl (2S,3S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-2-fluoro-3-phenylpropanoate 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以86%的产率得到(2S,3S)-3-Amino-2-fluoro-3-phenyl-propionic acid tert-butyl ester
  参考文献：
  名称：

  通过对映体纯 β-氨基烯醇化物的非对映选择性氟化来立体选择性合成 β-氨基-α-氟酯

  摘要：

  已经从肉桂酸叔丁酯和巴豆酸乙酯通过串联共轭加成 (S)-(-)-N-苄基-Na-甲基苄基酰胺，然后用N-氟苯磺酰亚胺。每个反应中形成的主要非对映异构体的绝对立体化学通过 X 射线晶体学证实。完全去保护得到 (2S,3S)-a-氟-b-苯丙氨酸，然后进行 Fmoc 保护。

  DOI：

  10.1055/s-2004-817782
• 作为产物：
  描述：

  tert-butyl (3R,αS)-3-(N-benzyl-N-α-methylbenzylamino)-3-phenylpropanoate 在 lithium diisopropyl amide 、 N-氟代双(对甲苯磺酰)胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.5h， 生成 t-butyl (2S,3S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-2-fluoro-3-phenylpropanoate 、 t-butyl (2R,3S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-2-fluoro-3-phenylpropanoate
  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.
• Stereoselective Synthesis of β-Amino-α-Fluoro Esters via Diastereoselective Fluorination of Enantiopure β-Amino Enolates
  作者：Peter J. Duggan、Philip C. Andrews、Vijaya Bhaskar、Karen M. Bromfield、Aileen M. Dodd、Sandhya A. Duggan、Tom D. McCarthy

  DOI：10.1055/s-2004-817782

  日期：——

  b-Amino-a-fluoro esters have been prepared stereoselec- tively from t-butyl cinnamate and ethyl crotonate via tandem conju- gate addition of lithium (S)-(-)-N-benzyl-N-a-methylbenzylamide, followed by fluorination with N-fluorobenzenesulfonimide. The absolute stereochemistry of the major diastereomers formed in each reaction was confirmed by X-ray crystallography. Complete depro- tection to give (2S

  已经从肉桂酸叔丁酯和巴豆酸乙酯通过串联共轭加成 (S)-(-)-N-苄基-Na-甲基苄基酰胺，然后用N-氟苯磺酰亚胺。每个反应中形成的主要非对映异构体的绝对立体化学通过 X 射线晶体学证实。完全去保护得到 (2S,3S)-a-氟-b-苯丙氨酸，然后进行 Fmoc 保护。