tert-butyl 3-[(3R,5S)-2-oxo-5-[(1S)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]oxolan-3-yl]propanoate | 674787-24-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl 3-[(3R,5S)-2-oxo-5-[(1S)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]oxolan-3-yl]propanoate
• CAS: 674787-24-7
• 化学式: C₂₇H₃₃NO₆
• 分子量: 467.562
• InChiKey: UHLGOXUUNIOEOR-VJBWXMMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-[(3R,5S)-2-oxo-5-[(1S)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]oxolan-3-yl]propanoate 在 palladium on activated charcoal 2-羟基吡啶 、 氢气 作用下， 以 乙醇 为溶剂， 反应 74.0h， 生成
  参考文献：
  名称：

  Rational design and synthesis of selective BACE-1 inhibitors

  摘要：

  An effective approach for enhancing the selectivity of beta-site amyloid precursor protein cleaving enzyme (BACE 1) inhibitors is developed based on the unique features of the S1' pocket of the enzyme. A series of low molecular weight ( < 600) compounds were synthesized with different moieties at the P1' position. The selectivity of BACE 1 inhibitors versus cathepsin D and renin was enhanced 120-fold by replacing the hydrophobic propyl group with a hydrophilic propionic acid group. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.061
• 作为产物：
  描述：

  phenylmethyl [(1S)-2-phenyl-1-[(2S)-tetrahydro-5-oxo-2-furanyl]ethyl]carbamate 在 ruthenium trichloride 、 sodium periodate 、 3> 、 硫酸 、 lithium hexamethyldisilazane 、 儿萘酚硼烷 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 四氯化碳 、 二氯甲烷 、 乙腈 为溶剂， 反应 64.0h， 生成 tert-butyl 3-[(3R,5S)-2-oxo-5-[(1S)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]oxolan-3-yl]propanoate
  参考文献：
  名称：

  Rational design and synthesis of selective BACE-1 inhibitors

  摘要：

  An effective approach for enhancing the selectivity of beta-site amyloid precursor protein cleaving enzyme (BACE 1) inhibitors is developed based on the unique features of the S1' pocket of the enzyme. A series of low molecular weight ( < 600) compounds were synthesized with different moieties at the P1' position. The selectivity of BACE 1 inhibitors versus cathepsin D and renin was enhanced 120-fold by replacing the hydrophobic propyl group with a hydrophilic propionic acid group. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.061

文献信息

• Rational design and synthesis of selective BACE-1 inhibitors
  作者：Stephen F. Brady、Satendra Singh、Ming-Chih Crouthamel、M.Katharine Holloway、Craig A. Coburn、Victor M. Garsky、Michael Bogusky、Michael W. Pennington、Joseph P. Vacca、Daria Hazuda、Ming-Tain Lai

  DOI：10.1016/j.bmcl.2003.11.061

  日期：2004.2

  An effective approach for enhancing the selectivity of beta-site amyloid precursor protein cleaving enzyme (BACE 1) inhibitors is developed based on the unique features of the S1' pocket of the enzyme. A series of low molecular weight ( < 600) compounds were synthesized with different moieties at the P1' position. The selectivity of BACE 1 inhibitors versus cathepsin D and renin was enhanced 120-fold by replacing the hydrophobic propyl group with a hydrophilic propionic acid group. (C) 2003 Elsevier Ltd. All rights reserved.