(4S,5R)-5-Allyl-4-(4-tert-butoxy-2,6-dimethyl-benzyl)-oxazolidin-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (4S,5R)-5-Allyl-4-(4-tert-butoxy-2,6-dimethyl-benzyl)-oxazolidin-2-one
• 英文别名: (4S,5R)-4-[[2,6-dimethyl-4-[(2-methylpropan-2-yl)oxy]phenyl]methyl]-5-prop-2-enyl-1,3-oxazolidin-2-one
• 化学式: C₁₉H₂₇NO₃
• 分子量: 317.428
• InChiKey: YTOIMEJQVYKEHN-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  [1-(4-tert-butoxy-2,6-dimethyl-benzyl)-2-hydroxy-pent-4-enyl]-carbamic acid tert-butyl ester 在 正丁基锂 、 potassium bromide 作用下， 以 四氢呋喃 为溶剂， 生成 (4S,5R)-5-Allyl-4-(4-tert-butoxy-2,6-dimethyl-benzyl)-oxazolidin-2-one
  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

文献信息

• 2,6-Dimethyltyrosine Analogues of a Stereodiversified Ligand Library:  Highly Potent, Selective, Non-Peptidic μ Opioid Receptor Agonists
  作者：Bryce A. Harrison、Gavril W. Pasternak、Gregory L. Verdine

  DOI：10.1021/jm025608s

  日期：2003.2.1

  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.