(2S,5S)-2-Benzyl-5-<(tert-butoxycarbonyl)amino>-6-phenyl-(E)-3-hexenoic acid | 155158-45-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (2S,5S)-2-Benzyl-5-<(tert-butoxycarbonyl)amino>-6-phenyl-(E)-3-hexenoic acid
• 英文别名: (2S,5S)-2-Benzyl-5-[(tert-butoxycarbonyl)amino]-6-phenyl-(E)-3-hexenoic acid；(E,2S,5S)-2-benzyl-5-[(2-methylpropan-2-yl)oxycarbonylamino]-6-phenylhex-3-enoic acid
• CAS: 155158-45-5
• 化学式: C₂₄H₂₉NO₄
• 分子量: 395.499
• InChiKey: UNWMFGNLNPXLNG-YBYKEUDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,5S)-2-Benzyl-5-<(tert-butoxycarbonyl)amino>-6-phenyl-(E)-3-hexenoic acid 在 间氯过氧苯甲酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 40.0h， 生成 Methyl (2S,3R,4R,5S)-2-benzyl-5-<(tert-butoxycarbonyl)amino>-3,4-epoxy-6-phenylhexanoate
  参考文献：
  名称：

  Stereoselective Epoxidation of Phe-Gly and Phe-Phe Vinyl Isosteres

  摘要：

  Novel Phe-Gly and Phe-Phe isosteres have been synthesized. Vinylic isosteres of Phe-Gly and Phe-Phe were prepared by facile Julia reactions, and the resulting stereoisomers were isolated and epoxidized (m-chloroperbenzoic acid). Observed stereoselectivities of epoxidation appear to emanate from a cooperative coordination of the incoming peracid by the carbamate group and the more weakly coordinating allylic ester function.

  DOI：

  10.1021/jo00084a037
• 作为产物：
  描述：

  2-Benzyl-3-<(tert-butyldimethylsilyl)oxy>-1-propanol 在 jones' reagent 、 草酰氯 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 0.5h， 生成 (2S,5S)-2-Benzyl-5-<(tert-butoxycarbonyl)amino>-6-phenyl-(E)-3-hexenoic acid
  参考文献：
  名称：

  Stereoselective Epoxidation of Phe-Gly and Phe-Phe Vinyl Isosteres

  摘要：

  Novel Phe-Gly and Phe-Phe isosteres have been synthesized. Vinylic isosteres of Phe-Gly and Phe-Phe were prepared by facile Julia reactions, and the resulting stereoisomers were isolated and epoxidized (m-chloroperbenzoic acid). Observed stereoselectivities of epoxidation appear to emanate from a cooperative coordination of the incoming peracid by the carbamate group and the more weakly coordinating allylic ester function.

  DOI：

  10.1021/jo00084a037

文献信息

• Stereoselective Epoxidation of Phe-Gly and Phe-Phe Vinyl Isosteres
  作者：Annika Jenmalm、Wei Berts、Yi-Lin Li、Kristina Luthman、Ingeborg Csoeregh、Uli Hacksell

  DOI：10.1021/jo00084a037

  日期：1994.3

  Novel Phe-Gly and Phe-Phe isosteres have been synthesized. Vinylic isosteres of Phe-Gly and Phe-Phe were prepared by facile Julia reactions, and the resulting stereoisomers were isolated and epoxidized (m-chloroperbenzoic acid). Observed stereoselectivities of epoxidation appear to emanate from a cooperative coordination of the incoming peracid by the carbamate group and the more weakly coordinating allylic ester function.