2,2,2-trichloroethyl N-(N-(L-alanyl)-N-methyl-L-phenylalanyl)-N-methylglycyl-L-isoleucinate hydrochloride | 1352449-59-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,2,2-trichloroethyl N-(N-(L-alanyl)-N-methyl-L-phenylalanyl)-N-methylglycyl-L-isoleucinate hydrochloride
• CAS: 1352449-59-2
• 化学式: C₂₄H₃₅Cl₃N₄O₅*ClH
• 分子量: 602.386
• InChiKey: ISMJFTXUJUHLHI-HBUCTZRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  37.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  122.04
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2,2,2-trichloroethyl N-(N-(L-alanyl)-N-methyl-L-phenylalanyl)-N-methylglycyl-L-isoleucinate hydrochloride 在 4-二甲氨基吡啶 、 氟化氢吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 2,2,2-trichloroethyl (2S,8S,11S,14R)-8-benzyl-2-((S)-sec-butyl)-14-(((2E,5S,6R,7S,8E)-7-hydroxy-2,6,8-trimethyl-5-((methylthio)methoxy)deca-2,8-dienoyl)oxy)-6,9,11,16-tetramethyl-4,7,10,13-tetraoxo-3,6,9,12-tetraazaheptadecanoate
  参考文献：
  名称：

  The total synthesis and structure–activity relationships of a highly cytotoxic depsipeptide kulokekahilide-2 and its analogs

  摘要：

  We successfully completed the total synthesis of kulokekahilide-2, a cytotoxic depsipeptide from the Cephalaspiedean mollusk Phillinopsis speciosa. We have revised the absolute stereochemistry of kulokekahilide-2 to 21-L-Ala, 24-D-MePhe, 37-L-Ile, 43-D-Ala, 15-D-Hica, and 5S,6S,7S-Dtda. We also investigated the cause of the mis-assignment of the configuration in the originally proposed kulokekahilide-2 and concluded that methanolysis using MeONa caused partial racemization, which led to the mis-assignment. The structure activity relationships of kulokekahilide-2 and its analogs indicate the importance of an L-amino acid at position 21. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.094
• 作为产物：
  描述：

  BOC-L-异亮氨酸 在 盐酸 、 4-二甲氨基吡啶 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 2,2,2-trichloroethyl N-(N-(L-alanyl)-N-methyl-L-phenylalanyl)-N-methylglycyl-L-isoleucinate hydrochloride
  参考文献：
  名称：

  The total synthesis and structure–activity relationships of a highly cytotoxic depsipeptide kulokekahilide-2 and its analogs

  摘要：

  We successfully completed the total synthesis of kulokekahilide-2, a cytotoxic depsipeptide from the Cephalaspiedean mollusk Phillinopsis speciosa. We have revised the absolute stereochemistry of kulokekahilide-2 to 21-L-Ala, 24-D-MePhe, 37-L-Ile, 43-D-Ala, 15-D-Hica, and 5S,6S,7S-Dtda. We also investigated the cause of the mis-assignment of the configuration in the originally proposed kulokekahilide-2 and concluded that methanolysis using MeONa caused partial racemization, which led to the mis-assignment. The structure activity relationships of kulokekahilide-2 and its analogs indicate the importance of an L-amino acid at position 21. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.094