(S)-ethyl 3-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazol-4-yl}-3-oxopropanoate | 205648-18-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (S)-ethyl 3-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazol-4-yl}-3-oxopropanoate
• 英文别名: ethyl 3-[5-methyl-2-[(1S)-1-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-1,3-oxazol-4-yl]-3-oxopropanoate
• CAS: 205648-18-6
• 化学式: C₁₆H₂₄N₂O₆
• 分子量: 340.376
• InChiKey: QDEHRTUFIDWKSF-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-ethyl 3-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazol-4-yl}-3-oxopropanoate 在 乙酸铵 、 lithium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 溶剂黄146 、 苯 为溶剂， 反应 27.0h， 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：

  (S)-2-(1-(tert-butoxycarbonylamino)ethyl)-5-methyloxazole-4-carboxylic acid 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 生成 (S)-ethyl 3-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazol-4-yl}-3-oxopropanoate
  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

文献信息

• 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 the Thiopeptide Promothiocin A
  作者：Mark C. Bagley、Katherine E. Bashford、Claire L. Hesketh、Christopher J. Moody

  DOI：10.1021/ja994247b

  日期：2000.4.1

  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.