dibenzyl [(2S)-3-[[(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]amino]-3-oxo-2-phenylmethoxypropyl] phosphate | 370867-66-6

• 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: dibenzyl [(2S)-3-[[(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]amino]-3-oxo-2-phenylmethoxypropyl] phosphate
• CAS: 370867-66-6
• 化学式: C₆₇H₇₇N₆O₁₅P
• 分子量: 1237.35
• InChiKey: KIYBSLPZNQVTSM-YWZHSFRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  89
• 可旋转键数：
  22
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  278
• 氢给体数：
  6
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  dibenzyl [(2S)-3-[[(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]amino]-3-oxo-2-phenylmethoxypropyl] phosphate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 水 为溶剂， 生成
  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：

  allyl L-phenylalaninate hydrochloride 在 palladium dihydroxide 、 四(三苯基膦)钯 吗啉 、 咪唑 、 盐酸 、 4-二甲氨基吡啶 、 phosphate buffer 、 氰基磷酸二乙酯 、 五氟苯基二苯基磷酸酯 、 氢气 、 溶剂黄146 、 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 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 二甲基亚砜 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 101.5h， 生成 dibenzyl [(2S)-3-[[(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]amino]-3-oxo-2-phenylmethoxypropyl] phosphate
  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.