N-(N-(((R)-2-(((2E,5S,6S,7S,8E)-7-((D-alanyl)oxy)-2,6,8-trimethyl-5-((methylthio)methoxy)deca-2,8-dienoyl)oxy)-4-methylpentanoyl)-L-alanyl)-N-methyl-L-phenylalanyl)-N-methylglycyl-L-isoleucine | 1075710-28-9

• 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: N-(N-(((R)-2-(((2E,5S,6S,7S,8E)-7-((D-alanyl)oxy)-2,6,8-trimethyl-5-((methylthio)methoxy)deca-2,8-dienoyl)oxy)-4-methylpentanoyl)-L-alanyl)-N-methyl-L-phenylalanyl)-N-methylglycyl-L-isoleucine
• CAS: 1075710-28-9
• 化学式: C₄₆H₇₃N₅O₁₁S
• 分子量: 904.179
• InChiKey: QRAJRYROGHSZEA-VBWQGZBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  63.0
• 可旋转键数：
  27.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  223.97
• 氢给体数：
  4.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  N-(N-(((R)-2-(((2E,5S,6S,7S,8E)-7-((D-alanyl)oxy)-2,6,8-trimethyl-5-((methylthio)methoxy)deca-2,8-dienoyl)oxy)-4-methylpentanoyl)-L-alanyl)-N-methyl-L-phenylalanyl)-N-methylglycyl-L-isoleucine 在 N-羟基-7-氮杂苯并三氮唑 、 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 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以70%的产率得到(3R,6S,12S,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
• 作为产物：
  描述：

  在 ammonium acetate 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 生成 N-(N-(((R)-2-(((2E,5S,6S,7S,8E)-7-((D-alanyl)oxy)-2,6,8-trimethyl-5-((methylthio)methoxy)deca-2,8-dienoyl)oxy)-4-methylpentanoyl)-L-alanyl)-N-methyl-L-phenylalanyl)-N-methylglycyl-L-isoleucine
  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