(2S)-N-[(2S,5S,8S,11R,12S,15S,18S,21R)-2,15-dibenzyl-8-[(2S)-butan-2-yl]-21-hydroxy-5-[(4-hydroxyphenyl)methyl]-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docosan-12-yl]-2-hydroxy-3-[oxido-bis(phenylmethoxy)phosphaniumyl]oxypropanamide | 370867-67-7

• 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: (2S)-N-[(2S,5S,8S,11R,12S,15S,18S,21R)-2,15-dibenzyl-8-[(2S)-butan-2-yl]-21-hydroxy-5-[(4-hydroxyphenyl)methyl]-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docosan-12-yl]-2-hydroxy-3-[oxido-bis(phenylmethoxy)phosphaniumyl]oxypropanamide
• CAS: 370867-67-7
• 化学式: C₆₀H₇₁N₆O₁₅P
• 分子量: 1147.23
• InChiKey: OGYBNBSLEHQHTK-ODNLILKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  82
• 可旋转键数：
  19
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  295
• 氢给体数：
  7
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  (2S)-N-[(2S,5S,8S,11R,12S,15S,18S,21R)-2,15-dibenzyl-8-[(2S)-butan-2-yl]-21-hydroxy-5-[(4-hydroxyphenyl)methyl]-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docosan-12-yl]-2-hydroxy-3-[oxido-bis(phenylmethoxy)phosphaniumyl]oxypropanamide 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 水 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 1.0h， 以89%的产率得到Phosphoric acid mono-{(S)-2-[(2S,5S,8S,11R,12S,15S,18S,21R)-2,15-dibenzyl-8-((S)-sec-butyl)-21-hydroxy-5-(4-hydroxy-benzyl)-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-10-oxa-1,4,7,14,17-pentaaza-bicyclo[16.3.1]docos-12-ylcarbamoyl]-2-hydroxy-ethyl} ester
  参考文献：
  名称：

  Synthetic studies of the cyclic depsipeptides bearing the 3-amino-6-hydroxy-2-piperidone (Ahp) unit. Total synthesis of the proposed structure of micropeptin T-20

  摘要：

  The first total synthesis of a cyclic depsipeptide possessing the 3-amino-6-hydroxy-2-piperidone (Ahp) unit was successfully IN achieved in a convergent manner by the oxidative construction of the Ahp unit at the later stage of the synthesis. This synthetic work provides data indicating that the structure of the target Ahp-depsipeptide, micropeptin T-20. should be re-examined. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.12.009
• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以95%的产率得到(2S)-N-[(2S,5S,8S,11R,12S,15S,18S,21R)-2,15-dibenzyl-8-[(2S)-butan-2-yl]-21-hydroxy-5-[(4-hydroxyphenyl)methyl]-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docosan-12-yl]-2-hydroxy-3-[oxido-bis(phenylmethoxy)phosphaniumyl]oxypropanamide
  参考文献：
  名称：

  Synthetic studies of the cyclic depsipeptides bearing the 3-amino-6-hydroxy-2-piperidone (Ahp) unit. Total synthesis of the proposed structure of micropeptin T-20

  摘要：

  The first total synthesis of a cyclic depsipeptide possessing the 3-amino-6-hydroxy-2-piperidone (Ahp) unit was successfully IN achieved in a convergent manner by the oxidative construction of the Ahp unit at the later stage of the synthesis. This synthetic work provides data indicating that the structure of the target Ahp-depsipeptide, micropeptin T-20. should be re-examined. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.12.009

文献信息

• Synthetic studies of micropeptin T-20, a novel 3-amino-6-hydroxy-2-piperidone (Ahp)-containing cyclic depsipeptide
  作者：Fumiaki Yokokawa、Akiko Inaizumi、Takayuki Shioiri

  DOI：10.1016/s0040-4039(01)01136-4

  日期：2001.8

  The synthetic studies of micropeptin T-20 including the late installation of the Ahp (3 -amino- 6-hydroxy-2-piperidone) residue through oxidation and cyclization of a homoserine to the requisite hemiaminal are described. (C) 2001 Elsevier Science Ltd. All rights reserved.