tert-butyl [(1S,2S)-1-benzyl-2-hydroxy-3-methoxypropyl]carbamate | 946420-60-6

• 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 [(1S,2S)-1-benzyl-2-hydroxy-3-methoxypropyl]carbamate
• 英文别名: tert-butyl N-[(2S,3S)-3-hydroxy-4-methoxy-1-phenylbutan-2-yl]carbamate
• CAS: 946420-60-6
• 化学式: C₁₆H₂₅NO₄
• 分子量: 295.379
• InChiKey: IMYOQXGBMIAJNE-UONOGXRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl [(1S,2S)-1-benzyl-2-hydroxy-3-methoxypropyl]carbamate 在 盐酸 、 迭氮酸 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 (2S,3R)-3-azido-4-methoxy-1-phenylbutan-2-amine hydrochloride
  参考文献：
  名称：

  Discovery of Isonicotinamide Derived β-Secretase Inhibitors:  In Vivo Reduction of β-Amyloid

  摘要：

  beta-Secretase inhibition offers an exciting opportunity for therapeutic intervention in the progression of Alzheimer's disease. A series of isonicotinamides derived from traditional aspartyl protease transition state isostere inhibitors has been optimized to yield low nanomolar inhibitors with sufficient penetration across the blood-brain barrier to demonstrate beta-amyloid lowering in a murine model.

  DOI：

  10.1021/jm070272d
• 作为产物：
  描述：

  甲醇 、 1-苄基-2,3-环氧正丙基-氨基甲酸叔丁酯 在 sodium hydride 作用下， 反应 17.0h， 以4.9 g的产率得到tert-butyl [(1S,2S)-1-benzyl-2-hydroxy-3-methoxypropyl]carbamate
  参考文献：
  名称：

  Discovery of Isonicotinamide Derived β-Secretase Inhibitors:  In Vivo Reduction of β-Amyloid

  摘要：

  beta-Secretase inhibition offers an exciting opportunity for therapeutic intervention in the progression of Alzheimer's disease. A series of isonicotinamides derived from traditional aspartyl protease transition state isostere inhibitors has been optimized to yield low nanomolar inhibitors with sufficient penetration across the blood-brain barrier to demonstrate beta-amyloid lowering in a murine model.

  DOI：

  10.1021/jm070272d

文献信息

• US5936104A
  申请人：——

  公开号：US5936104A

  公开（公告）日：1999-08-10
• Discovery of Isonicotinamide Derived β-Secretase Inhibitors:  In Vivo Reduction of β-Amyloid
  作者：Matthew G. Stanton、Shaun R. Stauffer、Alison R. Gregro、Melissa Steinbeiser、Philippe Nantermet、Sethu Sankaranarayanan、Eric A. Price、Guoxin Wu、Ming-Chih Crouthamel、Joan Ellis、Ming-Tain Lai、Amy S. Espeseth、Xiao-Ping Shi、Lixia Jin、Dennis Colussi、Beth Pietrak、Qian Huang、Min Xu、Adam J. Simon、Samuel L. Graham、Joseph P. Vacca、Harold Selnick

  DOI：10.1021/jm070272d

  日期：2007.7.1

  beta-Secretase inhibition offers an exciting opportunity for therapeutic intervention in the progression of Alzheimer's disease. A series of isonicotinamides derived from traditional aspartyl protease transition state isostere inhibitors has been optimized to yield low nanomolar inhibitors with sufficient penetration across the blood-brain barrier to demonstrate beta-amyloid lowering in a murine model.