tert-butyl (2S,3S)-3-(tertbutyldimethylsilyloxy)-4-hydroxy-1-phenylbutan-2-ylcarbamate | 1174892-46-6

• 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 (2S,3S)-3-(tertbutyldimethylsilyloxy)-4-hydroxy-1-phenylbutan-2-ylcarbamate
• 英文别名: tert-butyl N-[(2S,3S)-3-[tert-butyl(dimethyl)silyl]oxy-4-hydroxy-1-phenylbutan-2-yl]carbamate
• CAS: 1174892-46-6
• 化学式: C₂₁H₃₇NO₄Si
• 分子量: 395.615
• InChiKey: XNDRYPGITKYAQO-ZWKOTPCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.51
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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 (2S,3S)-3-(tertbutyldimethylsilyloxy)-4-hydroxy-1-phenylbutan-2-ylcarbamate 在 sodium carbonate 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以84%的产率得到(2S,3S)-3--2-<(tert-butyldimethylsilyl)oxy>-4-phenylbutanal
  参考文献：
  名称：

  A Potent and Orally Efficacious, Hydroxyethylamine-Based Inhibitor of β-Secretase

  摘要：

  beta-Secretase inhibitors are potentially disease-modifying treatments for Alzheimer's disease. Previous efforts in our laboratory have resulted in hydroxyethylamine-derived inhibitors such as 1 with low nanomolar potency against beta-site amyloid precursor protein cleaving enzyme (BACE). When dosed intravenously, compound 1 was also shown to significantly reduce A beta(40) levels in plasma, brain, and cerebral spinal fluid. Herein, we report further optimizations that led to the discovery of inhibitor 16 as a novel, potent, and orally efficacious BACE inhibitor.

  DOI：

  10.1021/ml3000148
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 在 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 四氢呋喃 为溶剂， 反应 14.17h， 以3.4 g的产率得到tert-butyl (2S,3S)-3-(tertbutyldimethylsilyloxy)-4-hydroxy-1-phenylbutan-2-ylcarbamate
  参考文献：
  名称：

  Stereoselective Synthesis ofanti-N-Protected 3-Amino-1,2-epoxides by Nucleophilic Addition toN-tert-Butanesulfinyl Imine of a Glyceraldehyde Synthon^†

  摘要：

  A di-O-TBS protected glyceraldellyde synthon was condensed with Ellman's reagent to form a bench-stable N-tert-butanesulfinyl imine 6, which served as a common intermediate for the stereoselective introduction Of various R groups. The Ellman adducts were converted to useful Multifunctional intermediates 18a-i in one pot. The alcohols 18a-i were efficiently elaborated to both known and novel anti-N-protected-3-amino-1,2-epoxides in two steps. Compound 2a is a key intermediate toward HIV protease inhibitors.

  DOI：

  10.1021/jo900643b