(S)-3-(2',6'-Dimethoxy-biphenyl-4-yl)-2-{[2-(2-hydroxy-ethyl)-tetrahydro-furan-2-carbonyl]-amino}-propionic acid tert-butyl ester | 327618-61-1

• 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: (S)-3-(2',6'-Dimethoxy-biphenyl-4-yl)-2-{[2-(2-hydroxy-ethyl)-tetrahydro-furan-2-carbonyl]-amino}-propionic acid tert-butyl ester
• CAS: 327618-61-1
• 化学式: C₂₈H₃₇NO₇
• 分子量: 499.604
• InChiKey: JHRFQHJVGWGAQI-QDLLFRBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  36.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  103.32
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-3-(2',6'-Dimethoxy-biphenyl-4-yl)-2-{[2-(2-hydroxy-ethyl)-tetrahydro-furan-2-carbonyl]-amino}-propionic acid tert-butyl ester 在 草酰氯 、 三乙酰氧基硼氢化钠 、 二甲基亚砜 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (2S)-3-[4-(2,6-dimethoxyphenyl)phenyl]-2-[[(2S)-2-[2-(dimethylamino)ethyl]oxolane-2-carbonyl]amino]propanoic acid
  参考文献：
  名称：

  Substituted tetrahydrofuroyl-1-phenylalanine derivatives as potent and specific VLA-4 antagonists

  摘要：

  A series of substituted tetra hydrofuroyl-1-phenylalanine derivatives was prepared and evaluated as VLA-4 antagonists. Substitution of the a carbon of the tetrahydrofuran with aryl groups increased the specificity for VLA-4 versus alpha(4)beta(7) while amide substitution increased the potency of the series without increasing the specificity. Substitution of the P carbon of the tetrahydrofuran with keto or amino groups slightly improved the specificity for VLA-4 versus alpha(4)beta(7) but with a significant loss in binding affinity for VLA-4. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00211-1
• 作为产物：
  描述：

  2-(2-tert-butyl-dimethylsilyl-oxyethyl)-2-tetrahydrofuroic acid, benzyl ester 在 palladium on activated charcoal 四丁基氟化铵 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 (S)-3-(2',6'-Dimethoxy-biphenyl-4-yl)-2-{[2-(2-hydroxy-ethyl)-tetrahydro-furan-2-carbonyl]-amino}-propionic acid tert-butyl ester
  参考文献：
  名称：

  Substituted tetrahydrofuroyl-1-phenylalanine derivatives as potent and specific VLA-4 antagonists

  摘要：

  A series of substituted tetra hydrofuroyl-1-phenylalanine derivatives was prepared and evaluated as VLA-4 antagonists. Substitution of the a carbon of the tetrahydrofuran with aryl groups increased the specificity for VLA-4 versus alpha(4)beta(7) while amide substitution increased the potency of the series without increasing the specificity. Substitution of the P carbon of the tetrahydrofuran with keto or amino groups slightly improved the specificity for VLA-4 versus alpha(4)beta(7) but with a significant loss in binding affinity for VLA-4. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00211-1