methyl 2-[2-[2-[(4S)-2,2-dimethyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-1,3-oxazolidin-4-yl]-1,3-thiazol-4-yl]-1,3-thiazol-4-yl]-5-phenyl-1,3-oxazole-4-carboxylate | 1445860-21-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 2-[2-[2-[(4S)-2,2-dimethyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-1,3-oxazolidin-4-yl]-1,3-thiazol-4-yl]-1,3-thiazol-4-yl]-5-phenyl-1,3-oxazole-4-carboxylate
• CAS: 1445860-21-8
• 化学式: C₂₇H₂₈N₄O₆S₂
• 分子量: 568.675
• InChiKey: CIFBNDSVNJRBMC-SFHVURJKSA-N

物化性质

• 沸点：
  730.3±70.0 °C(predicted)
• 密度：
  1.304±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  173
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl 2-[2-[2-[(4S)-2,2-dimethyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-1,3-oxazolidin-4-yl]-1,3-thiazol-4-yl]-1,3-thiazol-4-yl]-5-phenyl-1,3-oxazole-4-carboxylate 在 lithium hydroxide monohydrate 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 、 4-(4,6-二甲氧基三嗪-2-基)-4-甲基吗啉盐酸盐 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 methyl 2-[(Z)-1-[[(2S)-2-[[(2R,3S)-2-[[2-[2-[2-[(4S)-2,2-dimethyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-1,3-oxazolidin-4-yl]-1,3-thiazol-4-yl]-1,3-thiazol-4-yl]-5-phenyl-1,3-oxazole-4-carbonyl]amino]-3-methylpentanoyl]amino]propanoyl]amino]prop-1-enyl]-1,3-oxazole-4-carboxylate
  参考文献：
  名称：

  Total Synthesis and Biological Activity of Natural Product Urukthapelstatin A

  摘要：

  Herein we report the first total synthesis of the natural product Urkuthaplestatin A (Ustat A) utilizing a convergent synthetic strategy. The characterization and biological activity match those of the previously published natural product. Interestingly, several intermediates, including the linear and serine cyclized precursors, show a 100-fold decrease in cytotoxicity, with IC50's in the low micromolar range. These data indicate that the rigidity and the consecutive aromatic heterocyclic system are responsible for the biological activity.

  DOI：

  10.1021/ol401412v
• 作为产物：
  描述：

  (S)-(-)-3-BOC-4-甲氧羰基-2,2-二甲基-1,3-恶唑烷 在 劳森试剂 、 ammonium hydroxide 、 potassium hydrogencarbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 苯 为溶剂， 反应 51.33h， 生成 methyl 2-[2-[2-[(4S)-2,2-dimethyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-1,3-oxazolidin-4-yl]-1,3-thiazol-4-yl]-1,3-thiazol-4-yl]-5-phenyl-1,3-oxazole-4-carboxylate
  参考文献：
  名称：

  Total Synthesis and Biological Activity of Natural Product Urukthapelstatin A

  摘要：

  Herein we report the first total synthesis of the natural product Urkuthaplestatin A (Ustat A) utilizing a convergent synthetic strategy. The characterization and biological activity match those of the previously published natural product. Interestingly, several intermediates, including the linear and serine cyclized precursors, show a 100-fold decrease in cytotoxicity, with IC50's in the low micromolar range. These data indicate that the rigidity and the consecutive aromatic heterocyclic system are responsible for the biological activity.

  DOI：

  10.1021/ol401412v

文献信息

• Total Synthesis and Biological Activity of Natural Product Urukthapelstatin A
  作者：Chun-Chieh Lin、Worawan Tantisantisom、Shelli R. McAlpine

  DOI：10.1021/ol401412v

  日期：2013.7.19

  Herein we report the first total synthesis of the natural product Urkuthaplestatin A (Ustat A) utilizing a convergent synthetic strategy. The characterization and biological activity match those of the previously published natural product. Interestingly, several intermediates, including the linear and serine cyclized precursors, show a 100-fold decrease in cytotoxicity, with IC50's in the low micromolar range. These data indicate that the rigidity and the consecutive aromatic heterocyclic system are responsible for the biological activity.