methyl 2-(N-tert-butyloxycarbonylaminomethyl)-5-methyl-1,3-oxazole-4-carboxylate

• 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-(N-tert-butyloxycarbonylaminomethyl)-5-methyl-1,3-oxazole-4-carboxylate
• 英文别名: methyl 2-(tert-butoxycarbonylaminomethyl)-5-methyloxazole-4-carboxylate；Methyl 2-{[(tert-butoxycarbonyl)amino]methyl}-5-methyl-1,3-oxazole-4-carboxylate；methyl 5-methyl-2-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]-1,3-oxazole-4-carboxylate
• 化学式: C₁₂H₁₈N₂O₅
• 分子量: 270.285
• InChiKey: BCIONFINSWWLCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  90.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-(N-tert-butyloxycarbonylaminomethyl)-5-methyl-1,3-oxazole-4-carboxylate 在 水 作用下， 以 甲醇 、 水 为溶剂， 反应 17.0h， 以100%的产率得到2-(N-tert-butyloxycarbonylaminomethyl)-5-methyl-1,3-oxazole-4-carboxylic acid
  参考文献：
  名称：

  翻译后修饰的聚唑肽抗生素Goadsporin的全合成

  摘要：

  结构独特的聚吡咯抗生素戈德斯孔蛋白含有六个杂芳族恶唑环和噻唑环，这些环整合到氨基酸的线性阵列中，该氨基酸还包含两个脱氢丙氨酸残基。据报道，高效地合成了山羊孢子素，其中的关键步骤是使用铑（II）催化的重氮羰基化合物的反应生成四个恶唑环，这证明了铑卡宾化学在有机化学合成中的作用。

  DOI：

  10.1002/anie.201612103
• 作为产物：
  描述：

  2-Diazo-3-oxo-butyric acid methyl ester 在 dirhodium tetraacetate 、 碘 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 32.0h， 生成 methyl 2-(N-tert-butyloxycarbonylaminomethyl)-5-methyl-1,3-oxazole-4-carboxylate
  参考文献：
  名称：

  翻译后修饰的聚唑肽抗生素Goadsporin的全合成

  摘要：

  结构独特的聚吡咯抗生素戈德斯孔蛋白含有六个杂芳族恶唑环和噻唑环，这些环整合到氨基酸的线性阵列中，该氨基酸还包含两个脱氢丙氨酸残基。据报道，高效地合成了山羊孢子素，其中的关键步骤是使用铑（II）催化的重氮羰基化合物的反应生成四个恶唑环，这证明了铑卡宾化学在有机化学合成中的作用。

  DOI：

  10.1002/anie.201612103

文献信息

• Solution-Phase Synthesis of Linear and Cyclic Peptidomimetics Based on 2-Aminoalkyloxazole-4- or -5-carboxylates
  作者：Matthew O. Cox、Rolf H. Prager、Carina E. Svensson

  DOI：10.1071/ch03250

  日期：——

  The solution-phase synthesis of several small linear and cyclic peptidomimetics based on the coupling of BOC-protected 2-aminoalkyloxazole-4- or -5-carboxylic acids is reported. Cyclic amides have been formed both by sequential coupling and cyclization, or by cyclooligomerization.

  报告基于 BOC 保护的 2-氨基烷基恶唑-4-或-5-羧酸的偶联，溶液相合成了几种小型线性和环状拟肽化合物。环状酰胺是通过连续偶联和环化或环聚作用形成的。
• A mild high yielding synthesis of oxazole-4-carboxylate derivatives
  作者：Paula M.T. Ferreira、Elisabete M.S. Castanheira、Luís S. Monteiro、Goreti Pereira、Helena Vilaça

  DOI：10.1016/j.tet.2010.09.014

  日期：2010.11

  Several 2,5-disubstituted oxazole-4-carboxylates were prepared in high yields from the methyl esters of N-acyl-beta-halodehydroaminobutyric acid derivatives by treatment with a 2% solution of DBU in acetonitrile. The scope of this reaction was investigated and it was found that dehydrodipeptides having a beta-bromodehydroaminobutyric acid residue gave the corresponding oxazoles in good yields. The photophysical properties of some of the oxazoles prepared were studied in four solvents of different polarity. All compounds have reasonable high fluorescence quantum yields and a moderate solvent sensitivity, which makes them good candidates to be used as fluorescent probes. One of the fluorescent oxazoles prepared was inserted after cleavage of the methyl ester into two model peptides using a conventional solution phase strategy. The photophysical properties of the labelled peptides were studied in ethanol and water and compared with those of the oxazole. The results obtained showed that the oxazole maintains a good fluorescence level and the same solvent sensitivity when linked to a peptide chain. (C) 2010 Elsevier Ltd. All rights reserved.
• NOVEL ANTIBIOTICS
  申请人：PEOPLES Aaron

  公开号：US20120302613A1

  公开（公告）日：2012-11-29

  The invention relates generally to novel antibiotics and their analogs, to processes for the preparation of these novel antibiotics, to pharmaceutical compositions comprising the novel antibiotics; and to methods of using the novel antibiotics to treat or inhibit various disorders.
• Total Synthesis of the Post-translationally Modified Polyazole Peptide Antibiotic Goadsporin
  作者：Hannah L. Dexter、Huw E. L. Williams、William Lewis、Christopher J. Moody

  DOI：10.1002/anie.201612103

  日期：2017.3.6

  The structurally unique polyazole antibiotic goadsporin contains six heteroaromatic oxazole and thiazole rings integrated into a linear array of amino acids that also contains two dehydroalanine residues. An efficient total synthesis of goadsporin is reported in which the key steps are the use of rhodium(II)‐catalyzed reactions of diazocarbonyl compounds to generate the four oxazole rings, which demonstrates

  结构独特的聚吡咯抗生素戈德斯孔蛋白含有六个杂芳族恶唑环和噻唑环，这些环整合到氨基酸的线性阵列中，该氨基酸还包含两个脱氢丙氨酸残基。据报道，高效地合成了山羊孢子素，其中的关键步骤是使用铑（II）催化的重氮羰基化合物的反应生成四个恶唑环，这证明了铑卡宾化学在有机化学合成中的作用。