ethyl 2-[(1S)-1-[[5-methyl-2-[[[(2S)-3-methyl-2-[[2-[2-[5-methyl-2-[(1S)-1-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-1,3-oxazol-4-yl]-6-(phenylmethoxymethyl)pyridin-3-yl]-1,3-thiazole-4-carbonyl]amino]butanoyl]amino]methyl]-1,3-oxazole-4-carbonyl]amino]ethyl]-1,3-thiazole-4-carboxylate | 216480-99-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-[(1S)-1-[[5-methyl-2-[[[(2S)-3-methyl-2-[[2-[2-[5-methyl-2-[(1S)-1-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-1,3-oxazol-4-yl]-6-(phenylmethoxymethyl)pyridin-3-yl]-1,3-thiazole-4-carbonyl]amino]butanoyl]amino]methyl]-1,3-oxazole-4-carbonyl]amino]ethyl]-1,3-thiazole-4-carboxylate
• CAS: 216480-99-8
• 化学式: C₄₇H₅₅N₉O₁₀S₂
• 分子量: 970.14
• InChiKey: IJDSBRPMUBMRFX-UXVOWUFOSA-N

物化性质

• 熔点：
  88-90 °C
• 密度：
  1.285±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  68
• 可旋转键数：
  22
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  308
• 氢给体数：
  4
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  ethyl 2-[(1S)-1-[[5-methyl-2-[[[(2S)-3-methyl-2-[[2-[2-[5-methyl-2-[(1S)-1-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-1,3-oxazol-4-yl]-6-(phenylmethoxymethyl)pyridin-3-yl]-1,3-thiazole-4-carbonyl]amino]butanoyl]amino]methyl]-1,3-oxazole-4-carbonyl]amino]ethyl]-1,3-thiazole-4-carboxylate 在 lithium hydroxide 、 水 作用下， 以 四氢呋喃 为溶剂， 以97%的产率得到2-((S)-1-{[2-({(S)-2-[(2-{6-Benzyloxymethyl-2-[2-((S)-1-tert-butoxycarbonylamino-ethyl)-5-methyl-oxazol-4-yl]-pyridin-3-yl}-thiazole-4-carbonyl)-amino]-3-methyl-butyrylamino}-methyl)-5-methyl-oxazole-4-carbonyl]-amino}-ethyl)-thiazole-4-carboxylic acid
  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
• 作为产物：
  描述：

  (S)-2-(1-(tert-butoxycarbonylamino)ethyl)-5-methyloxazole-4-carboxylic acid 在 劳森试剂 、 N-甲基吗啉 、 2,6-二甲基吡啶 、 乙酸铵 、 lithium hydroxide 、 potassium hydrogencarbonate 、 三乙胺 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 乙醇 、 溶剂黄146 、 苯 为溶剂， 反应 51.91h， 生成 ethyl 2-[(1S)-1-[[5-methyl-2-[[[(2S)-3-methyl-2-[[2-[2-[5-methyl-2-[(1S)-1-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-1,3-oxazol-4-yl]-6-(phenylmethoxymethyl)pyridin-3-yl]-1,3-thiazole-4-carbonyl]amino]butanoyl]amino]methyl]-1,3-oxazole-4-carbonyl]amino]ethyl]-1,3-thiazole-4-carboxylate
  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

• The first synthesis of promothiocin A
  作者：Christopher J. Moody、Mark C. Bagley

  DOI：10.1039/a805762a

  日期：——

  The first total synthesis of the naturally occurring macrocyclic thiopeptide promothiocin A 1 is described.

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