(4S,5S)-trans-N-<(tert-butyloxy)carbonyl>-5-amino-4-hydroxy-6-phenylhex-2-enoic acid | 99113-32-3

• 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: (4S,5S)-trans-N-<(tert-butyloxy)carbonyl>-5-amino-4-hydroxy-6-phenylhex-2-enoic acid
• 英文别名: (E,4S,5S)-4-hydroxy-5-[(2-methylpropan-2-yl)oxycarbonylamino]-6-phenylhex-2-enoic acid
• CAS: 99113-32-3
• 化学式: C₁₇H₂₃NO₅
• 分子量: 321.373
• InChiKey: STBFFAHSLSUDHD-KYXFNPKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (4S,5S)-trans-N-<(tert-butyloxy)carbonyl>-5-amino-4-hydroxy-6-phenylhex-2-enoic acid 以 甲醇 、 乙醚 为溶剂， 以97%的产率得到(4S,5S)-5-[(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenyl-(E)-2-hexenoate
  参考文献：
  名称：

  A highly stereoselective synthesis of (E)-alkene dipeptide isosteres via organocyanocopper-Lewis acid mediation reaction

  摘要：

  A stereoselective synthesis of protected (E)-alkene dipeptide isosteres by the reaction of the mesylates of homochiral delta-aminated gamma-hydroxy (E)-alpha,beta-enoates with either RCu(CN)Li.BF3 or RCu(CN)MgX.BF3 reagent is described. The degree of diastereoselectivity has been found to be uniformly high except for the serine- and threonine-derived acetonides 77 and 81. The synthesis permits the introduction of sterically hindered appendages such as isopropyl and tert-butyl groups at the alpha position to the ester group. This methodology provides a new route to a wide range of modified (E)-alkene peptide mimics that may have biological importance.

  DOI：

  10.1021/jo00014a010
• 作为产物：
  描述：

  (3S,4S)-N-[(tert-Butyloxy)carbonyl]-4-amino-3-acetoxy-5-phenylpentene 、 乙氧甲酰基亚甲基三苯基膦 在 sodium hydroxide 、 二甲基硫 、 臭氧 作用下， 生成 (4S,5S)-trans-N-<(tert-butyloxy)carbonyl>-5-amino-4-hydroxy-6-phenylhex-2-enoic acid
  参考文献：
  名称：

  Synthesis of new dipeptide analogs containing novel ketovinyl and hydroxyethylidene isosteres via Grignard addition to chiral .alpha.-amino aldehydes

  摘要：

  DOI：

  10.1021/jo00225a085

文献信息

• A highly stereoselective synthesis of (E)-alkene dipeptide isosteres via organocyanocopper-Lewis acid mediation reaction
  作者：Toshiro Ibuka、Hiromu Habashita、Akira Otaka、Nobutaka Fujii、Yusaku Oguchi、Tadao Uyehara、Yoshinori Yamamoto

  DOI：10.1021/jo00014a010

  日期：1991.7

  A stereoselective synthesis of protected (E)-alkene dipeptide isosteres by the reaction of the mesylates of homochiral delta-aminated gamma-hydroxy (E)-alpha,beta-enoates with either RCu(CN)Li.BF3 or RCu(CN)MgX.BF3 reagent is described. The degree of diastereoselectivity has been found to be uniformly high except for the serine- and threonine-derived acetonides 77 and 81. The synthesis permits the introduction of sterically hindered appendages such as isopropyl and tert-butyl groups at the alpha position to the ester group. This methodology provides a new route to a wide range of modified (E)-alkene peptide mimics that may have biological importance.
• Synthesis of new dipeptide analogs containing novel ketovinyl and hydroxyethylidene isosteres via Grignard addition to chiral .alpha.-amino aldehydes
  作者：Gunnar J. Hanson、Thomas Lindberg

  DOI：10.1021/jo00225a085

  日期：1985.12