2-benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-2,6-dimethyl-phenyl)-3,7-dihydroxy-non-4-enoic acid | 503186-61-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 2-benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-2,6-dimethyl-phenyl)-3,7-dihydroxy-non-4-enoic acid
• CAS: 503186-61-6
• 化学式: C₃₃H₄₇NO₇
• 分子量: 569.739
• InChiKey: MKJOMKAEAKHEFQ-LBNVTSAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.53
• 重原子数：
  41.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  125.32
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-2,6-dimethyl-phenyl)-3,7-dihydroxy-non-4-enoic acid 在 三异丙基硅烷 、 二甲基氨基丙基乙基碳酰胺 、 1-羟基苯并三唑 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 17.0h， 生成 2,6-dihydroxy-1-(4-hydroxy-2,6-dimethyl-benzyl)-7-phenethylcarbamoyl-8-phenyl-oct-4-enyl-ammonium
  参考文献：
  名称：

  2,6-Dimethyltyrosine Analogues of a Stereodiversified Ligand Library:  Highly Potent, Selective, Non-Peptidic μ Opioid Receptor Agonists

  摘要：

  We recently reported the use of an exhaustively stereodiversified library based on endomorphin-2 (1) to discovery opioid receptor (MOR) ligands of type 2-4. Here, we report the synthesis and evaluation of 2,6-dimethyltyrosine analogues 5-10. These analogues showed improved affinity for MOR relative to 2-4. In the cases of 5 and 6, we synthesized and evaluated five stereoisomers of each, thereby discovering stereoisomers with unexpected potency, selectivity, and efficacy. These results illustrate the utility of acyclic, stereodiverse libraries.

  DOI：

  10.1021/jm025608s
• 作为产物：
  描述：

  2-benzyl-3-hydroxy-pent-4-enethioic S-benzyl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 2-benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-2,6-dimethyl-phenyl)-3,7-dihydroxy-non-4-enoic acid
  参考文献：
  名称：

  2,6-Dimethyltyrosine Analogues of a Stereodiversified Ligand Library:  Highly Potent, Selective, Non-Peptidic μ Opioid Receptor Agonists

  摘要：

  We recently reported the use of an exhaustively stereodiversified library based on endomorphin-2 (1) to discovery opioid receptor (MOR) ligands of type 2-4. Here, we report the synthesis and evaluation of 2,6-dimethyltyrosine analogues 5-10. These analogues showed improved affinity for MOR relative to 2-4. In the cases of 5 and 6, we synthesized and evaluated five stereoisomers of each, thereby discovering stereoisomers with unexpected potency, selectivity, and efficacy. These results illustrate the utility of acyclic, stereodiverse libraries.

  DOI：

  10.1021/jm025608s