(S)-4-(tert-butoxycarbonylamino)-5-phenyl-1-trimethylsilylpent-1-yn-3-one | 321164-87-8

• 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: (S)-4-(tert-butoxycarbonylamino)-5-phenyl-1-trimethylsilylpent-1-yn-3-one
• 英文别名: tert-butyl N-[(2S)-3-oxo-1-phenyl-5-trimethylsilylpent-4-yn-2-yl]carbamate
• CAS: 321164-87-8
• 化学式: C₁₉H₂₇NO₃Si
• 分子量: 345.514
• InChiKey: FJZPSGKDRGNXQE-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.57
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-4-(tert-butoxycarbonylamino)-5-phenyl-1-trimethylsilylpent-1-yn-3-one 在 dimethyl sulfide borane 、 (S)-B-methyl-4,5,5-triphenyl-1,3,2-oxazaborolidine 、 bis(cyclohexanyl)borane 作用下， 以 四氢呋喃 为溶剂， 生成 (3R,4S)-4-(tert-butoxycarbonylamino)-3-hydroxy-5-phenylpentanoic acid
  参考文献：
  名称：

  A Synthetic Approach to 3-Hydroxy 4-Substituted Carboxylic Acids based on the Stereoselective Reduction of 1-Trimethylsilyl-1-alkyn-3-ones

  摘要：

  The oxazaborolidine-mediated reduction of chiral, 4-substituted 1-trimethylsilyl-1-alkyn-3-ones followed by hydroboration affords syn or anti 3-hydroxy 4-substituted carboxylic acids, common substructures of a number of biologically active macrolides, peptides and depsipeptides, with high control on the new C(3) stereocenter. This strategy has been applied to the synthesis of (3S,4S)-3-hydroxy-4-methylheptanoic acid and of N-Boc-statine, constituents of permentin A and pepstatin, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00905-4
• 作为产物：
  描述：

  BOC-PHE-甲氧基甲胺 、 三甲基乙炔基硅 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.17h， 以50%的产率得到(S)-4-(tert-butoxycarbonylamino)-5-phenyl-1-trimethylsilylpent-1-yn-3-one
  参考文献：
  名称：

  A Synthetic Approach to 3-Hydroxy 4-Substituted Carboxylic Acids based on the Stereoselective Reduction of 1-Trimethylsilyl-1-alkyn-3-ones

  摘要：

  The oxazaborolidine-mediated reduction of chiral, 4-substituted 1-trimethylsilyl-1-alkyn-3-ones followed by hydroboration affords syn or anti 3-hydroxy 4-substituted carboxylic acids, common substructures of a number of biologically active macrolides, peptides and depsipeptides, with high control on the new C(3) stereocenter. This strategy has been applied to the synthesis of (3S,4S)-3-hydroxy-4-methylheptanoic acid and of N-Boc-statine, constituents of permentin A and pepstatin, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00905-4