(S)-2-(4-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazolyl})-6-methylpyridine-3-thiocarboxamide | 271597-81-0

• 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)-2-(4-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazolyl})-6-methylpyridine-3-thiocarboxamide
• 英文别名: tert-butyl N-[(1S)-1-[4-(3-carbamothioyl-6-methylpyridin-2-yl)-5-methyl-1,3-oxazol-2-yl]ethyl]carbamate
• CAS: 271597-81-0
• 化学式: C₁₈H₂₄N₄O₃S
• 分子量: 376.48
• InChiKey: DQBIPXHNKZITRC-JTQLQIEISA-N

物化性质

• 密度：
  1.208±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  135
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-溴丙酮酸乙酯 、 (S)-2-(4-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazolyl})-6-methylpyridine-3-thiocarboxamide 以 乙二醇二甲醚 为溶剂， 反应 2.0h， 以31%的产率得到(S)-2-(4-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazolyl})-3-(4-ethoxycarbonyl-2-thiazolyl)-6-methylpyridine
  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-(4-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazolyl})-6-methylpyridine-3-carboxylic acid 在 劳森试剂 、 ammonium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 73.58h， 生成 (S)-2-(4-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazolyl})-6-methylpyridine-3-thiocarboxamide
  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

• 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.