(S)-methyl 2-(1-((tert-butoxycarbonyl)amino)-2-phenylethyl)-5-methyloxazole-4-carboxylate | 1257861-35-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-methyl 2-(1-((tert-butoxycarbonyl)amino)-2-phenylethyl)-5-methyloxazole-4-carboxylate
• 英文别名: methyl (S)-2-(1-(tert-butoxycarbonylamino)-2-phenylethyl)-5-methyloxazole-4-carboxylate；methyl 2-[1-(tert-butoxycarbonylamino)-2-phenylethyl]-5-methyloxazole-4-carboxylate；methyl 2-{(1S)-1-[(tert-butoxycarbonyl)amino]-2-phenylethyl}-5-methyl-1,3-oxazole-4-carboxylate；methyl 5-methyl-2-[(1S)-1-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylethyl]-1,3-oxazole-4-carboxylate
• CAS: 1257861-35-0
• 化学式: C₁₉H₂₄N₂O₅
• 分子量: 360.41
• InChiKey: UAPJVKWWSWEZKE-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  (S)-methyl 2-(1-((tert-butoxycarbonyl)amino)-2-phenylethyl)-5-methyloxazole-4-carboxylate 在 lithium hydroxide monohydrate 、 N,N-二异丙基乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 197.0h， 生成 wewakazole B
  参考文献：
  名称：

  合成细胞毒性的氰基维菌素，Wewakazole B

  摘要：

  我们在这里报告了通过有效的溶液相方法细胞毒性的氰基actin，Wewakazole B的合成。合成的关键步骤是线性十二肽的大环内酰胺化和两个带有三个不同取代恶唑环的六肽的构建。

  DOI：

  10.1016/j.tetlet.2017.02.012
• 作为产物：
  描述：

  methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-3-oxobutanoate 在 碘 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以84%的产率得到(S)-methyl 2-(1-((tert-butoxycarbonyl)amino)-2-phenylethyl)-5-methyloxazole-4-carboxylate
  参考文献：
  名称：

  环状十二肽Wewakazole和Wewakazole B的全合成

  摘要：

  环状十二肽wewakazole和wewakazole B通过不同的策略，通过常见的含有tris-脯氨酸的恶唑八肽和两个单独的bis-恶唑的四肽单元合成，然后进行肽偶联和大环化。这三个恶唑氨基酸片段可通过重氮羰基化合物的铑（II）催化的酰胺N–H插入，或铑类化合物与腈的环加成而容易地获得。

  DOI：

  10.1021/acs.orglett.7b01393

文献信息

• Total synthesis of wewakazole B
  作者：Bohua Long、Jingzhao Zhang、Xudong Tang、Zhengzhi Wu

  DOI：10.1039/c6ob01783e

  日期：——

  Wewakazole B is a novel cyclodecapeptide with highly potent cytotoxic activity isolated from a sample of M. producens collected from the Red Sea. It contains nine common and three modified amino acid residues. The first total synthesis of Wewakazole B was successfully achieved on a gram scale, unambiguously confirming its structure. Notable features include the careful choice of amino acid-protecting

  Wewakazole B是一种新型的环十肽，具有很强的细胞毒活性，是从红海生产的M. Produces样品中分离出来的。它包含九个常见和三个修饰的氨基酸残基。Wewakazole B的第一个全合成成功地达到了克级，明确证实了其结构。显着特征包括仔细选择氨基酸保护基团和构建该天然产物中存在的三种不同的取代恶唑。
• 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.