2-benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-phenyl)-3,6-dihydroxy-non-4-enethioic acid S-benzyl ester | 507277-19-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-phenyl)-3,6-dihydroxy-non-4-enethioic acid S-benzyl ester
• CAS: 507277-19-2
• 化学式: C₃₈H₄₉NO₆S
• 分子量: 647.876
• InChiKey: LSBIGPFFKXGUFH-HFJAUBSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.29
• 重原子数：
  46.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  105.09
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-phenyl)-3,6-dihydroxy-non-4-enethioic acid S-benzyl ester 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以84%的产率得到2-benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-phenyl)-3,6-dihydroxy-non-4-enoic acid
  参考文献：
  名称：

  Unpredictable Stereochemical Preferences for Mu Opioid Receptor Activity in an Exhaustively Stereodiversified Library of 1,4-Enediols

  摘要：

  [GRAPHICS]Using olefin cross-metathesis, we synthesized a novel stereodiversified library of compounds 3 containing a trans-1,4-enediol. Screening this library for mu opioid receptor (MOR) affinity identified multiple high-affinity ligands and revealed that the stereochemical configuration varied widely among those ligands having the highest affinity. It was not possible to predict the configurations of the most active compounds 3 on the basis of the configuration of endomorphin-2, a known MOR peptide ligand, validating the diversity-based approach to ligand discovery.

  DOI：

  10.1021/ol027237f
• 作为产物：
  描述：

  methyl (3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-[4-[(2-methylpropan-2-yl)oxy]phenyl]butanoate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.5h， 生成 2-benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-phenyl)-3,6-dihydroxy-non-4-enethioic acid S-benzyl ester
  参考文献：
  名称：

  Unpredictable Stereochemical Preferences for Mu Opioid Receptor Activity in an Exhaustively Stereodiversified Library of 1,4-Enediols

  摘要：

  [GRAPHICS]Using olefin cross-metathesis, we synthesized a novel stereodiversified library of compounds 3 containing a trans-1,4-enediol. Screening this library for mu opioid receptor (MOR) affinity identified multiple high-affinity ligands and revealed that the stereochemical configuration varied widely among those ligands having the highest affinity. It was not possible to predict the configurations of the most active compounds 3 on the basis of the configuration of endomorphin-2, a known MOR peptide ligand, validating the diversity-based approach to ligand discovery.

  DOI：

  10.1021/ol027237f