(3S,4S,5R,6S)-4-Acetoxy-6-acetylamino-5-tert-butoxycarbonylamino-1-(2-ethyl-butyl)-piperidine-3-carboxylic acid methyl ester | 315700-18-6

• 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: (3S,4S,5R,6S)-4-Acetoxy-6-acetylamino-5-tert-butoxycarbonylamino-1-(2-ethyl-butyl)-piperidine-3-carboxylic acid methyl ester
• CAS: 315700-18-6
• 化学式: C₂₂H₃₉N₃O₇
• 分子量: 457.568
• InChiKey: XUZGCSVYZPKEMG-VJANTYMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.81
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  123.27
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (3S,4S,5R,6S)-4-Acetoxy-6-acetylamino-5-tert-butoxycarbonylamino-1-(2-ethyl-butyl)-piperidine-3-carboxylic acid methyl ester 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 以76%的产率得到(5S,6S)-6-Acetylamino-5-tert-butoxycarbonylamino-1-(2-ethyl-butyl)-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester
  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：

  (3S,4S,5R,6S)-4-Acetoxy-6-acetylamino-5-tert-butoxycarbonylamino-piperidine-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester 在 palladium on activated charcoal 氢气 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 (3S,4S,5R,6S)-4-Acetoxy-6-acetylamino-5-tert-butoxycarbonylamino-1-(2-ethyl-butyl)-piperidine-3-carboxylic acid methyl ester
  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