(2S,3S)-2-acetamido-1-(2-ethylbutanoyl)-3-hydroxy-3,6-dihydro-2H-pyridine-5-carboxylic acid | 315700-23-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (2S,3S)-2-acetamido-1-(2-ethylbutanoyl)-3-hydroxy-3,6-dihydro-2H-pyridine-5-carboxylic acid
• CAS: 315700-23-3
• 化学式: C₁₄H₂₂N₂O₅
• 分子量: 298.339
• InChiKey: XEUJFHAVBRRMMT-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-acetamido-1-(2-ethylbutanoyl)-3-hydroxy-3,6-dihydro-2H-pyridine-5-carboxylic acid 在 sodium tetrahydroborate 、 迭氮酸 、 戴斯-马丁氧化剂 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 、 苯 为溶剂， 生成 6-acetamido-5-amino-3,4-dehydro-N-(2-ethylbutyryl)-3-piperidinecarboxylic acid
  参考文献：
  名称：

  Synthesis of 6-Acetamido-5-amino- and -5-guanidino-3,4-dehydro-N-(2-ethylbutyryl)- 3-piperidinecarboxylic Acids Related to Zanamivir and Oseltamivir, Inhibitors of Influenza Virus Neuraminidases

  摘要：

  [GRAPHICS]6-Acetamido-5-amino- and -5-guanidino-3,4-dehydro-N-(2-ethylbutyryl)-3-piperidinecarboxylic acids (8 end 9) have been synthesized starting from natural siastatin a, a bacterial neuraminidase inhibitor isolated from Streptomyces culture in a stereospecific fashion. These compounds are related to zanamivir and oseltamivir, inhibitors of influenza virus neuraminidases.

  DOI：

  10.1021/ol000261d
• 作为产物：
  描述：

  (5S,6S)-6-Acetylamino-1-(2-ethyl-butyryl)-5-(2-ethyl-butyryloxy)-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以100%的产率得到(2S,3S)-2-acetamido-1-(2-ethylbutanoyl)-3-hydroxy-3,6-dihydro-2H-pyridine-5-carboxylic acid
  参考文献：
  名称：

  Synthesis of 6-Acetamido-5-amino- and -5-guanidino-3,4-dehydro-N-(2-ethylbutyryl)- 3-piperidinecarboxylic Acids Related to Zanamivir and Oseltamivir, Inhibitors of Influenza Virus Neuraminidases

  摘要：

  [GRAPHICS]6-Acetamido-5-amino- and -5-guanidino-3,4-dehydro-N-(2-ethylbutyryl)-3-piperidinecarboxylic acids (8 end 9) have been synthesized starting from natural siastatin a, a bacterial neuraminidase inhibitor isolated from Streptomyces culture in a stereospecific fashion. These compounds are related to zanamivir and oseltamivir, inhibitors of influenza virus neuraminidases.

  DOI：

  10.1021/ol000261d

文献信息

• Synthesis of 6-Acetamido-5-amino- and -5-guanidino-3,4-dehydro-<i>N</i>-(2-ethylbutyryl)- 3-piperidinecarboxylic Acids Related to Zanamivir and Oseltamivir, Inhibitors of Influenza Virus Neuraminidases
  作者：Eiki Shitara、Yoshio Nishimura、Kuniaki Nerome、Yasuaki Hiramoto、Tomio Takeuchi

  DOI：10.1021/ol000261d

  日期：2000.11.1

  [GRAPHICS]6-Acetamido-5-amino- and -5-guanidino-3,4-dehydro-N-(2-ethylbutyryl)-3-piperidinecarboxylic acids (8 end 9) have been synthesized starting from natural siastatin a, a bacterial neuraminidase inhibitor isolated from Streptomyces culture in a stereospecific fashion. These compounds are related to zanamivir and oseltamivir, inhibitors of influenza virus neuraminidases.