ethyl 2-((4S,5R)-5-methyl-2-oxooxazolidin-4-yl)thiazole-4-carboxylate | 190523-42-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 2-((4S,5R)-5-methyl-2-oxooxazolidin-4-yl)thiazole-4-carboxylate
• 英文别名: ethyl 2-[(4S,5R)-5-methyl-2-oxo-1,3-oxazolidin-4-yl]-1,3-thiazole-4-carboxylate
• CAS: 190523-42-3
• 化学式: C₁₀H₁₂N₂O₄S
• 分子量: 256.282
• InChiKey: NKTWCIMCZWYRRT-VDTYLAMSSA-N

物化性质

• 熔点：
  133-134 °C
• 沸点：
  490.1±38.0 °C(Predicted)
• 密度：
  1.323±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 2-((4S,5R)-5-methyl-2-oxooxazolidin-4-yl)thiazole-4-carboxylate 在 盐酸 、 4-二甲氨基吡啶 、 lithium hydroxide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 14.76h， 生成 ethyl 2-[(1R)-1-[[2-[(Z)-1-[[(2S,3R)-2-amino-3-hydroxybutanoyl]amino]prop-1-enyl]-1,3-thiazole-4-carbonyl]amino]-2-methylpropyl]-1,3-thiazole-4-carboxylate
  参考文献：
  名称：

  Synthesis of the Bycroft−Gowland Structure of Micrococcin P1

  摘要：

  [GRAPHICS]We describe the chemical synthesis of the accepted structure of micrococcin P1, a member of the thiostrepton group of antibiotics, and we show that this architecture does not correspond to that of the natural product. Methods developed during the present study should greatly facilitate ongoing efforts centering on the determination of the actual structure of microccin P1, in addition to being applicable to the synthesis of more complex thiostrepton congeners.

  DOI：

  10.1021/ol991115e
• 作为产物：
  描述：

  methyl (4S,5R)-5-methyl-2-oxooxazolidine-4-carboxylate 在 劳森试剂 、 氨 作用下， 以 乙醇 为溶剂， 生成 ethyl 2-((4S,5R)-5-methyl-2-oxooxazolidin-4-yl)thiazole-4-carboxylate
  参考文献：
  名称：

  Studies toward Thiostrepton Antibiotics:  Assembly of the Central Pyridine−Thiazole Cluster of Micrococcins

  摘要：

  DOI：

  10.1021/jo9704422

文献信息

• Total Synthesis and Stereochemical Assignment of Micrococcin P1
  作者：David Lefranc、Marco A. Ciufolini

  DOI：10.1002/anie.200900621

  日期：2009.5.25

  Fifty years after the discovery of the thiopeptide antibiotic micrococcin P1, the constitutional and stereochemical uncertainties concerning its structure have been lifted with its total synthesis and absolute stereochemical assignment (see picture).

  发现硫肽抗生素微球菌素P1五十年后，通过其总合成和绝对立体化学分配，消除了有关其结构的组成和立体化学不确定性（见图）。
• Synthetic studies on the thiostrepton family of peptide antibiotics: synthesis of the tetrasubstituted dehydropiperidine and piperidine cores
  作者：Syuhei Higashibayashi、Kimiko Hashimoto、Masaya Nakata

  DOI：10.1016/s0040-4039(01)02090-1

  日期：2002.1

  The tetrasubstituted dehydropiperidine and piperidine cores of the thiostrepton family of peptide antibiotics were synthesized which featured the coupling between the azomethine ylide and the enantiopure sulfinimine, and the subsequent stereoselective reduction of the six-membered imine.

  合成了肽抗生素的硫代链霉菌素家族的四取代的脱氢哌啶和哌啶核心，其特征在于偶氮甲碱内酯和对映体亚磺酰胺之间的偶联，以及随后的六元亚胺的立体选择性还原。
• Studies toward Thiostrepton Antibiotics:  Assembly of the Central Pyridine−Thiazole Cluster of Micrococcins
  作者：Marco A. Ciufolini、Yong Chun Shen

  DOI：10.1021/jo9704422

  日期：1997.6.13
• Synthesis of the Bycroft−Gowland Structure of Micrococcin P1
  作者：Marco A. Ciufolini、Yong-Chun Shen

  DOI：10.1021/ol991115e

  日期：1999.12.1

  [GRAPHICS]We describe the chemical synthesis of the accepted structure of micrococcin P1, a member of the thiostrepton group of antibiotics, and we show that this architecture does not correspond to that of the natural product. Methods developed during the present study should greatly facilitate ongoing efforts centering on the determination of the actual structure of microccin P1, in addition to being applicable to the synthesis of more complex thiostrepton congeners.