ethyl 2-((tert-butyl)diphenylsilyloxymethyl)thiazole-4-carboxylate | 318471-43-1

• 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-((tert-butyl)diphenylsilyloxymethyl)thiazole-4-carboxylate
• 英文别名: Ethyl 2-(((tert-butyldiphenylsilyl)oxy)methyl)thiazole-4-carboxylate；ethyl 2-[[tert-butyl(diphenyl)silyl]oxymethyl]-1,3-thiazole-4-carboxylate
• CAS: 318471-43-1
• 化学式: C₂₃H₂₇NO₃SSi
• 分子量: 425.624
• InChiKey: XBMHTHTYDZDQSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  76.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-((tert-butyl)diphenylsilyloxymethyl)thiazole-4-carboxylate 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-(((tert-Butyldiphenylsilyl)oxy)methyl)thiazole-4-carbaldehyde
  参考文献：
  名称：

  Regioselective synthesis of fluoroaldols. Studies toward fluoroepothilones syntheses via antibody catalysis

  摘要：

  A general method for the synthesis of fluoromethyl aldols has been developed. Tributylboron enolates of fluoroacetone react with thiazole aldehydes (6) to provide fluoromethylaldols (4) regioselectively in high yields. Regioisomeric fluoroaldols (5) are produced as a 1:1 isomeric mixture of the erythro and three products via a two-step procedure: first, aldol reaction with Weinreb amide and then Grignard reaction. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)01469-6
• 作为产物：
  描述：

  3-溴丙酮酸乙酯 、 2-{[(tert-butyl)(diphenyl)silyl]oxy}ethanethioamide 以 苯 为溶剂， 反应 1.0h， 生成 ethyl 2-((tert-butyl)diphenylsilyloxymethyl)thiazole-4-carboxylate
  参考文献：
  名称：

  Regioselective synthesis of fluoroaldols. Studies toward fluoroepothilones syntheses via antibody catalysis

  摘要：

  A general method for the synthesis of fluoromethyl aldols has been developed. Tributylboron enolates of fluoroacetone react with thiazole aldehydes (6) to provide fluoromethylaldols (4) regioselectively in high yields. Regioisomeric fluoroaldols (5) are produced as a 1:1 isomeric mixture of the erythro and three products via a two-step procedure: first, aldol reaction with Weinreb amide and then Grignard reaction. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)01469-6

文献信息

• Discovery of Novel Thieno[2,3-d]pyrimidin-4-yl Hydrazone-Based Cyclin-Dependent Kinase 4 Inhibitors: Synthesis, Biological Evaluation and Structure-Activity Relationships
  作者：Takao Horiuchi、Yasuyuki Takeda、Noriyasu Haginoya、Masaki Miyazaki、Motoko Nagata、Mayumi Kitagawa、Kouichi Akahane、Kouichi Uoto

  DOI：10.1248/cpb.59.991

  日期：——

  The design, synthesis, and evaluation of novel thieno[2,3-d]pyrimidin-4-yl hydrazone analogues as cyclin-dependent kinase 4 (CDK4) inhibitors are described. In continuing our program aim to search for potent CDK4 inhibitors, the introduction of a thiazole group at the hydrazone part has led to marked enhancement of chemical stability. Furthermore, by focusing on the optimization at the C-4' position

  描述，设计和合成新型噻吩并[2,3-d]嘧啶-4-基类似物作为细胞周期蛋白依赖性激酶4（CDK4）抑制剂。在继续我们的计划以寻找有效的CDK4抑制剂的过程中，在part部分引入噻唑基团导致化学稳定性显着提高。此外，通过集中于噻唑环的C-4'位置和噻吩并[2,3-d]嘧啶部分的C-6位置的优化，已确定化合物35在HCT116异种移植模型中有效细胞。在本文中，我们对合成化合物的效价，选择性和结构活性关系进行了讨论。
• Total Synthesis of Thiostrepton. Assembly of Key Building Blocks and Completion of the Synthesis
  作者：K. C. Nicolaou、Mark Zak、Brian S. Safina、Anthony A. Estrada、Sang Hyup Lee、Marta Nevalainen

  DOI：10.1021/ja052934z

  日期：2005.8.1

  completion of the total synthesis of thiostrepton (1) is described. The synthesis proceeded from key building blocks 2-5, which were assembled into a growing substrate that finally led to the target molecule. Thus, the dehydropiperidine peptide core 2 was, after appropriate manipulation, coupled to the thiazoline-thiazole fragment 3, and the resulting product was advanced to intermediate 11 possessing the

  描述了硫链丝菌肽 (1) 的全合成完成。合成从关键的构建块 2-5 开始，它们被组装成一个不断增长的基质，最终形成目标分子。因此，脱氢哌啶肽核心2在适当操作后与噻唑啉-噻唑片段3偶联，所得产物被推进为具有噻唑啉-噻唑大环的中间体11。然后将双脱氢丙氨酸尾等价物 4 和喹哪二酸片段 5 依次掺入，并将如此获得的产物进一步精制以形成分子的第二个大环。沿途遇到的几个障碍被系统地调查和克服，最终开辟了道路，通过中间体 20、32、44、45 和 46，到达目标天然产物 1。