(2R,3R)-2-(t-butoxycarbonylamino)-3-cyclopentyl-3-hydroxypropanoic acid | 578717-94-9

• 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: (2R,3R)-2-(t-butoxycarbonylamino)-3-cyclopentyl-3-hydroxypropanoic acid
• CAS: 578717-94-9
• 化学式: C₁₃H₂₃NO₅
• 分子量: 273.329
• InChiKey: IILUSGCAJRQYOX-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.52
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  95.86
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2-(t-butoxycarbonylamino)-3-cyclopentyl-3-hydroxypropanoic acid 在 20 % Pd(OH)2/C 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 、 甲苯 为溶剂， 50.0~80.0 ℃ 、101.33 kPa 条件下， 反应 5.0h， 生成 (3R)-1-butyl-2,5-dioxo-3-((1R)-1-hydroxy-1-cyclopentylmethyl)-1,4,9-triazaspiro[5.5]undecane hydrochloride
  参考文献：
  名称：

  Discovery of 4-[4-({(3R)-1-butyl-3-[(R)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undec-9-yl}methyl)phenoxy]benzoic acid hydrochloride: A highly potent orally available CCR5 selective antagonist

  摘要：

  Based on the original spirodiketopiperazine design framework, further optimization of an orally available CCR5 antagonist was undertaken. Structural hybridization of the hydroxylated analog 4 derived from one of the oxidative metabolites and the new orally available non-hydroxylated benzoic acid analog 5 resulted in another potent orally available CCR5 antagonist 6a as a clinical candidate. Full details of a structure-activity relationship (SAR) study and ADME properties are presented. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.022
• 作为产物：
  描述：

  (2S,3R)-3-cyclopentyloxirane-2-carbaldehyde 在 sodium hypochlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 20 % Pd(OH)2/C 、 氢气 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 10.5h， 生成 (2R,3R)-2-(t-butoxycarbonylamino)-3-cyclopentyl-3-hydroxypropanoic acid
  参考文献：
  名称：

  Discovery of 4-[4-({(3R)-1-butyl-3-[(R)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undec-9-yl}methyl)phenoxy]benzoic acid hydrochloride: A highly potent orally available CCR5 selective antagonist

  摘要：

  Based on the original spirodiketopiperazine design framework, further optimization of an orally available CCR5 antagonist was undertaken. Structural hybridization of the hydroxylated analog 4 derived from one of the oxidative metabolites and the new orally available non-hydroxylated benzoic acid analog 5 resulted in another potent orally available CCR5 antagonist 6a as a clinical candidate. Full details of a structure-activity relationship (SAR) study and ADME properties are presented. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.022