benzyl N-(hydroxymethyl)-N-[(2R,3S)-1,1,1-trifluoro-2-hydroxy-4-methylpentan-3-yl]carbamate | 1247868-81-0

• 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: benzyl N-(hydroxymethyl)-N-[(2R,3S)-1,1,1-trifluoro-2-hydroxy-4-methylpentan-3-yl]carbamate
• CAS: 1247868-81-0
• 化学式: C₁₅H₂₀F₃NO₄
• 分子量: 335.323
• InChiKey: NBKMQXHBUDPRAT-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  benzyl (4S,5R)-5-hydroxy-4-(propan-2-yl)-5-(trifluoromethyl)-1,3-oxazolidine-3-carboxylate 在 sodium tetrahydroborate 作用下， 以 乙醇 、 水 为溶剂， 生成 benzyl N-(hydroxymethyl)-N-[(2S,3S)-1,1,1-trifluoro-2-hydroxy-4-methylpentan-3-yl]carbamate 、 benzyl N-(hydroxymethyl)-N-[(2R,3S)-1,1,1-trifluoro-2-hydroxy-4-methylpentan-3-yl]carbamate
  参考文献：
  名称：

  Stereoselective synthesis of chiral β-amino trifluoromethyl alcohol: development of a manufacturing process for a key intermediate in the production of a novel elastase inhibitor, AE-3763

  摘要：

  We have successfully synthesized chiral beta-amino trifluoromethyl alcohol (2S,3S)-7a, which is a key intermediate in the production of AE-3763, by stereoselective reduction of N-Cbz-protected 5-hydroxy-5-(trifluoromethyl)-1,3-oxazolidine 4 prepared from L-valine in 3 steps followed by alkaline hydrolysis. This new method can be applied to the industrial-scale synthesis of AE-3763. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.06.038

文献信息

• Stereoselective synthesis of chiral β-amino trifluoromethyl alcohol: development of a manufacturing process for a key intermediate in the production of a novel elastase inhibitor, AE-3763
  作者：Yasunao Inoue、Tomoki Omodani、Ryotaro Shiratake、Fuminori Sato

  DOI：10.1016/j.tetasy.2010.06.038

  日期：2010.8

  We have successfully synthesized chiral beta-amino trifluoromethyl alcohol (2S,3S)-7a, which is a key intermediate in the production of AE-3763, by stereoselective reduction of N-Cbz-protected 5-hydroxy-5-(trifluoromethyl)-1,3-oxazolidine 4 prepared from L-valine in 3 steps followed by alkaline hydrolysis. This new method can be applied to the industrial-scale synthesis of AE-3763. (C) 2010 Elsevier Ltd. All rights reserved.