(3R,6S,12S,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 | 1009642-77-6

• 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: (3R,6S,12S,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
• CAS: 1009642-77-6
• 化学式: C₄₄H₆₇N₅O₁₀
• 分子量: 826.043
• InChiKey: JUJXAYASADIXIM-ZNOWDLDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  59
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  201
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  Boc-N-甲基-L-苯丙氨酸 在 2,6-二甲基吡啶 、 盐酸 、 4-二甲氨基吡啶 、 N-羟基-7-氮杂苯并三氮唑 、 ammonium acetate 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 水 、 1-羟基苯并三唑 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 氟化氢吡啶 、 silver nitrate 、 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 、 锌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 32.5h， 生成 (3R,6S,12S,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

文献信息

• The total synthesis and structure–activity relationships of a highly cytotoxic depsipeptide kulokekahilide-2 and its analogs
  作者：Yuuki Takada、Masahiro Umehara、Ryosuke Katsumata、Yoichi Nakao、Junji Kimura

  DOI：10.1016/j.tet.2011.10.094

  日期：2012.1

  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.