N-(N-(((R)-2-(((2E,5S,6S,7S,8E)-7-(((((9H-fluoren-9-yl)methoxy)carbonyl)-L-alanyl)oxy)-2,6,8-trimethyl-5-((methylthio)methoxy)deca-2,8-dienoyl)oxy)-4-methylpentanoyl)-D-alanyl)-N-methyl-L-phenylalanyl)-N-methylglycyl-L-isoleucine | 1352449-50-3

• 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: N-(N-(((R)-2-(((2E,5S,6S,7S,8E)-7-(((((9H-fluoren-9-yl)methoxy)carbonyl)-L-alanyl)oxy)-2,6,8-trimethyl-5-((methylthio)methoxy)deca-2,8-dienoyl)oxy)-4-methylpentanoyl)-D-alanyl)-N-methyl-L-phenylalanyl)-N-methylglycyl-L-isoleucine
• CAS: 1352449-50-3
• 化学式: C₆₁H₈₃N₅O₁₃S
• 分子量: 1126.42
• InChiKey: WJBCPNLTGUWOBH-VNJQDQRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.08
• 重原子数：
  80.0
• 可旋转键数：
  30.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  236.28
• 氢给体数：
  4.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  N-(N-(((R)-2-(((2E,5S,6S,7S,8E)-7-(((((9H-fluoren-9-yl)methoxy)carbonyl)-L-alanyl)oxy)-2,6,8-trimethyl-5-((methylthio)methoxy)deca-2,8-dienoyl)oxy)-4-methylpentanoyl)-D-alanyl)-N-methyl-L-phenylalanyl)-N-methylglycyl-L-isoleucine 在 二乙胺 作用下， 以 乙腈 为溶剂， 以98%的产率得到
  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 、 锌 作用下， 以 四氢呋喃 、 水 为溶剂， 以84%的产率得到N-(N-(((R)-2-(((2E,5S,6S,7S,8E)-7-(((((9H-fluoren-9-yl)methoxy)carbonyl)-L-alanyl)oxy)-2,6,8-trimethyl-5-((methylthio)methoxy)deca-2,8-dienoyl)oxy)-4-methylpentanoyl)-D-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