[(2S)-1-oxo-1-phenylmethoxypropan-2-yl] (2R,3R)-2-methyl-3-[[2-[(1S)-1-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-1,3-thiazole-4-carbonyl]amino]hexanoate | 927438-81-1

• 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: [(2S)-1-oxo-1-phenylmethoxypropan-2-yl] (2R,3R)-2-methyl-3-[[2-[(1S)-1-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-1,3-thiazole-4-carbonyl]amino]hexanoate
• CAS: 927438-81-1
• 化学式: C₂₈H₃₉N₃O₇S
• 分子量: 561.7
• InChiKey: YFIYYGYAHBBNAD-XODKDNOYSA-N

物化性质

• 沸点：
  705.0±60.0 °C(predicted)
• 密度：
  1.183±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  39
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  161
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2S)-1-oxo-1-phenylmethoxypropan-2-yl] (2R,3R)-2-methyl-3-[[2-[(1S)-1-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-1,3-thiazole-4-carbonyl]amino]hexanoate 在 palladium on activated charcoal 氢气 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 [(2S)-1-[methyl-[(2S)-1-[methyl-[(2S)-3-methyl-1-[(2-methylpropan-2-yl)oxy]-1-oxobutan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-1-oxopropan-2-yl] (2R,3R)-2-methyl-3-[[2-[(1S)-1-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-1,3-thiazole-4-carbonyl]amino]hexanoate
  参考文献：
  名称：

  ulongamide A的全合成，一种从海洋蓝细菌Lyngbya sp。分离的环状二肽。

  摘要：

  ulongamide A（1）是一种具有细胞毒性的天然环状二肽肽，是通过一条收敛性路线实现的，该路线涉及将片段7和8与五肽24偶联，然后在先去除t- Boc保护基团之后将其环化。

  DOI：

  10.1016/j.tetlet.2006.11.117
• 作为产物：
  描述：

  (S)-(-)-乳酸苄酯 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 [(2S)-1-oxo-1-phenylmethoxypropan-2-yl] (2R,3R)-2-methyl-3-[[2-[(1S)-1-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-1,3-thiazole-4-carbonyl]amino]hexanoate
  参考文献：
  名称：

  Synthesis of O-Me Ulongamide B and O-Me Ulongamide C, Natural Modified Cyclodepsipeptides

  摘要：

  Synthesis of O-Me ulongamide B and O-Me ulongamide C, modified natural cyclodepsipeptides, was achieved by a convergent route. The respective dipeptides and tridepsipeptides were coupled, obtaining linear depsipentapeptides, which were then deprotected and cyclized. These compounds were tested against three different types of human carcinoma cells and showed only moderate activity.

  DOI：

  10.1080/00397911.2011.618284

文献信息

• Synthesis of <i>O</i>-Me Ulongamide B and <i>O</i>-Me Ulongamide C, Natural Modified Cyclodepsipeptides
  作者：Cuauhtémoc Alvarado、Gerardo Hernández、Eduardo Díaz、José D. Soano、Miguel A. Vilchis-Reyes、Miguel A. Martínez-Urbina、Angel Guzmán

  DOI：10.1080/00397911.2011.618284

  日期：2013.3.1

  Synthesis of O-Me ulongamide B and O-Me ulongamide C, modified natural cyclodepsipeptides, was achieved by a convergent route. The respective dipeptides and tridepsipeptides were coupled, obtaining linear depsipentapeptides, which were then deprotected and cyclized. These compounds were tested against three different types of human carcinoma cells and showed only moderate activity.
• Total synthesis of ulongamide A, a cyclic depsipeptide isolated from marine cyanobacteria Lyngbya sp.
  作者：Cuauhtémoc Alvarado、Eduardo Díaz、Ángel Guzmán

  DOI：10.1016/j.tetlet.2006.11.117

  日期：2007.1

  A total synthesis of ulongamide A (1), a cytotoxic natural cyclic depsipeptide, was achieved by a convergent route involving coupling of the fragments 7 and 8 to the pentapeptide 24, and subsequent cyclization thereof after prior removal of the t-Boc protecting groups.

  ulongamide A（1）是一种具有细胞毒性的天然环状二肽肽，是通过一条收敛性路线实现的，该路线涉及将片段7和8与五肽24偶联，然后在先去除t- Boc保护基团之后将其环化。