(5S,6S)-6-Acetylamino-1-(2-ethyl-butyryl)-5-hydroxy-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid benzhydryl ester | 315700-24-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (5S,6S)-6-Acetylamino-1-(2-ethyl-butyryl)-5-hydroxy-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid benzhydryl ester
• CAS: 315700-24-4
• 化学式: C₂₇H₃₂N₂O₅
• 分子量: 464.561
• InChiKey: YMBYEEBIRQLFAA-ZCYQVOJMSA-N

物化性质

• 沸点：
  686.9±55.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  95.94
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (5S,6S)-6-Acetylamino-1-(2-ethyl-butyryl)-5-hydroxy-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid benzhydryl ester 在 sodium tetrahydroborate 、 迭氮酸 、 戴斯-马丁氧化剂 、 三苯基膦 、 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 (5S,6S)-6-Acetylamino-5-amino-1-(2-ethyl-butyryl)-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid benzhydryl 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：

  (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， 生成 (5S,6S)-6-Acetylamino-1-(2-ethyl-butyryl)-5-hydroxy-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid benzhydryl 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

文献信息

• Synthesis and biological evaluation of gem-diamine 1-N-iminosugars related to l-iduronic acid as inhibitors of heparan sulfate 2-O-sulfotransferase
  作者：Jillian R. Brown、Yoshio Nishimura、Jeffrey D. Esko

  DOI：10.1016/j.bmcl.2005.10.055

  日期：2006.2

  A variety of gem-diamine 1-N-iminosugars related to L-iduronic acid were synthesized and evaluated as inhibitors of heparan sulfate uronyl 2-O-sulfotransferase using an in vitro enzyme assay. Two iminosugars containing guanidino groups acted as potent inhibitors of the enzyme. (c) 2005 Elsevier Ltd. All rights reserved.