(3S,6S,12R,15S,18R,24S,25S,26S,E)-12-benzyl-26-((E)-but-2-en-2-yl)-6-((S)-sec-butyl)-18-isobutyl-3,10,13,15,21,25-hexamethyl-24-((methylthio)methoxy)-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacos-21-ene-2,5,8,11,14,17,20-heptaone | 1352449-57-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: (3S,6S,12R,15S,18R,24S,25S,26S,E)-12-benzyl-26-((E)-but-2-en-2-yl)-6-((S)-sec-butyl)-18-isobutyl-3,10,13,15,21,25-hexamethyl-24-((methylthio)methoxy)-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacos-21-ene-2,5,8,11,14,17,20-heptaone
• CAS: 1352449-57-0
• 化学式: C₄₆H₇₁N₅O₁₀S
• 分子量: 886.163
• InChiKey: AGTJSCSWVIVWSS-VKIWBSDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.58
• 重原子数：
  62.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  189.75
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (3S,6S,12R,15S,18R,24S,25S,26S,E)-12-benzyl-26-((E)-but-2-en-2-yl)-6-((S)-sec-butyl)-18-isobutyl-3,10,13,15,21,25-hexamethyl-24-((methylthio)methoxy)-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacos-21-ene-2,5,8,11,14,17,20-heptaone 在 2,6-二甲基吡啶 、 水 、 silver nitrate 作用下， 以 四氢呋喃 为溶剂， 以98%的产率得到(3S,6S,12R,15S,18R,21E,24S,25S,26S)-12-benzyl-6-[(2S)-butan-2-yl]-26-[(E)-but-2-en-2-yl]-24-hydroxy-3,10,13,15,21,25-hexamethyl-18-(2-methylpropyl)-1,19-dioxa-4,7,10,13,16-pentazacyclohexacos-21-ene-2,5,8,11,14,17,20-heptone
  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：

  2,2,2-trichloroethyl (2S,3S)-2-[[2-[[(2R)-2-[[(2S)-2-[[(2R)-2-hydroxy-4-methylpentanoyl]amino]propanoyl]-methylamino]-3-phenylpropanoyl]-methylamino]acetyl]amino]-3-methylpentanoate 在 吡啶 、 4-二甲氨基吡啶 、 N-羟基-7-氮杂苯并三氮唑 、 ammonium acetate 、 氟化氢吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 二乙胺 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 57.5h， 生成 (3S,6S,12R,15S,18R,24S,25S,26S,E)-12-benzyl-26-((E)-but-2-en-2-yl)-6-((S)-sec-butyl)-18-isobutyl-3,10,13,15,21,25-hexamethyl-24-((methylthio)methoxy)-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacos-21-ene-2,5,8,11,14,17,20-heptaone
  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