methyl (S)-2-(1-(tert-butoxycarbonylamino)ethyl)-5-methyloxazole-4-carboxylate | 205648-16-4

• 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 (S)-2-(1-(tert-butoxycarbonylamino)ethyl)-5-methyloxazole-4-carboxylate
• 英文别名: (S)-methyl 2-(1-((tert-butoxycarbonyl)amino)ethyl)-5-methyloxazole-4-carboxylate；methyl 5-methyl-2-[(1S)-1-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-1,3-oxazole-4-carboxylate
• CAS: 205648-16-4
• 化学式: C₁₃H₂₀N₂O₅
• 分子量: 284.312
• InChiKey: VGNBDTKLNWOFIN-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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 (S)-2-(1-(tert-butoxycarbonylamino)ethyl)-5-methyloxazole-4-carboxylate 在 乙酸铵 、 lithium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 溶剂黄146 、 苯 为溶剂， 反应 32.33h， 生成 (S)-2-(4-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazolyl})-6-methylpyridine-3-carboxylic acid
  参考文献：
  名称：

  Total Synthesis of the Thiopeptide Promothiocin A

  摘要：

  The thiopeptide (or thiostrepton) antibiotics are a class of sulfur-containing highly modified cyclic peptides with interesting biological activity. Described herein is the total synthesis of the thiopeptide antibiotic promothiocin A, which utilizes a modified Bohlmann-Rahtz pyridine synthesis to establish the oxazolyl-thiazole-pyridine heterocyclic centerpiece of the antibiotic. The oxazole building blocks were obtained by a dirhodium(II)-catalyzed chemoselective carbenoid N-H insertion reaction followed by cyclodehydration, and the thiazoles by the Hantzsch reaction. Two different strategies for macrocyclization were successfully employed, with the dehydroalanine side chain of the natural product being introduced in the last steps of the synthesis.

  DOI：

  10.1021/ja994247b
• 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， 生成 methyl (S)-2-(1-(tert-butoxycarbonylamino)ethyl)-5-methyloxazole-4-carboxylate
  参考文献：
  名称：

  The first synthesis of promothiocin A

  摘要：

  描述了天然存在的大环硫肽promothiocin A 1 的首次全合成。

  DOI：

  10.1039/a805762a

文献信息

• Total Synthesis of the Cyclic Dodecapeptides Wewakazole and Wewakazole B
  作者：Martyn Inman、Hannah L. Dexter、Christopher J. Moody

  DOI：10.1021/acs.orglett.7b01393

  日期：2017.7.7

  tetrapeptide units, followed by peptide coupling and macrocyclization. The three oxazole amino acid fragments are readily accessible by rhodium(II)-catalyzed amide N–H insertion of diazocarbonyl compounds, or by the cycloaddition of rhodium carbenoids with nitriles.

  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。
• Unified Azoline and Azole Syntheses by Optimized Aza-Wittig Chemistry
  作者：Patrick Loos、Cyril Ronco、Matthias Riedrich、Hans-Dieter Arndt

  DOI：10.1002/ejoc.201300160

  日期：2013.6

  Intramolecular aza-Wittig ring closures were applied to synthesize thiazolines, oxazolines, and imidazolines from β-azido thioester, ester, and amide precursors. The cyclization precursors were obtained from amino acid derivatives. Optimized conditions for diazo transfer with a fast rate and racemization suppression, (thio)esterification, and amide coupling reactions are described. The ring closure reaction can

  分子内 aza-Wittig 环闭合用于从 β-叠氮基硫酯、酯和酰胺前体合成噻唑啉、恶唑啉和咪唑啉。环化前体是从氨基酸衍生物中获得的。描述了具有快速和外消旋化抑制、（硫代）酯化和酰胺偶联反应的重氮转移的优化条件。闭环反应可以在中性条件下用 PPh3 进行，并且发现对五元环具有高度的化学选择性。如果酰胺基团被甲苯磺酰基激活，则亚氨基膦的分子内闭环会提供具有位置特异性甲苯磺酰基保护的对映纯咪唑啉产品。
• Synthesis of cytotoxic cyanobactin, Wewakazole B
  作者：Kiranmai Nayani、SD. Anwar Hussaini

  DOI：10.1016/j.tetlet.2017.02.012

  日期：2017.3

  We report herein the synthesis of cytotoxic cyanobactin, Wewakazole B through an efficient solution-phase approach. The key steps of the synthesis are the macrocyclic lactamization of linear dodecapeptide and construction of two hexapeptides with three different substituted oxazole rings.

  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。
• Studies on Thiopeptide Antibiotics: Synthesis of an Oxazole-Thiazole-Pyridine Fragment related to Promothiocin A
  作者：Christopher J. Moody、Mark C. Bagley

  DOI：10.1055/s-1998-1670

  日期：1998.4

  Promothiocin A 1, isolated from Streptomyces sp. SF2741, is a member of the thiopeptide family of antibiotics. These antibiotics, which inhibit protein synthesis in bacteria and induce the expression of various genes (of unknown function), are characterised by their complex structure in which an array of heterocyclic rings is incorporated into a macrocyclic peptide framework. Despite the fascinating biological activity of the thiopeptide antibiotics, very little synthetic work has been carried out to date, although the synthesis of the pyridine fragments of the micrococcins, sulfomycin and nosiheptide has been addressed recently, as has the construction of some related pyridines. In continuation of our interest in the synthesis of heterocyclic natural products, we now report the synthesis of the oxazole-thiazole-pyridine 2, which contains the required functionality for elaboration into promothiocin A 1.

  从链霉菌SF2741中分离得到的普罗莫西辛A 1，属于硫肽类抗生素家族。这类抗生素通过抑制细菌蛋白质合成并诱导多种未知功能基因的表达，其特点在于复杂的结构中，一系列杂环结构被整合到一个大环肽骨架中。尽管硫肽类抗生素具有引人注目的生物活性，但迄今为止，关于其合成的工作非常有限。虽然最近已解决微球菌素、硫霉素和诺西肽的吡啶片段的合成问题，以及一些相关吡啶结构的构建，但整体合成进展仍显不足。继我们对杂环天然产物合成的兴趣之后，我们现在报道了含有呋喃-噻唑-吡啶结构的化合物2的合成，该结构含有进一步合成普罗莫西辛A 1所需的功能基团。
• 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。