(2R,4S,5S)-2-Allyl-5-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-phenyl-hexanoic acid | 674787-21-4

• 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: (2R,4S,5S)-2-Allyl-5-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-phenyl-hexanoic acid
• 英文别名: (2R,4S,5S)-4-[tert-butyl(dimethyl)silyl]oxy-5-[(2-methylpropan-2-yl)oxycarbonylamino]-6-phenyl-2-prop-2-enylhexanoic acid
• CAS: 674787-21-4
• 化学式: C₂₆H₄₃NO₅Si
• 分子量: 477.717
• InChiKey: NTUNZNABIZBSBN-FSSWDIPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.18
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,4S,5S)-2-Allyl-5-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-phenyl-hexanoic acid 在 palladium on activated charcoal N-甲基吗啉 、 盐酸 、 乙二胺四乙酸 、 氢气 、 1-羟基苯并三唑 作用下， 以 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 62.33h， 生成 (S)-N-((1S,2S,4R)-1-Benzyl-2-hydroxy-4-isobutylcarbamoyl-heptyl)-2-(3-methyl-butyrylamino)-succinamic acid
  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：

  tert-butyl (1S)-1-[(2S)-5-oxotetrahydrofuran-2-yl]-2-phenylethylcarbamate 在 咪唑 、 lithium hydroxide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.5h， 生成 (2R,4S,5S)-2-Allyl-5-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-phenyl-hexanoic acid
  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