(S)-5-benzyloxy-4-methyl-1-trimethylsilylpent-1-yn-3-one | 214273-22-0

• 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: (S)-5-benzyloxy-4-methyl-1-trimethylsilylpent-1-yn-3-one
• 英文别名: (4S)-4-methyl-5-phenylmethoxy-1-trimethylsilylpent-1-yn-3-one
• CAS: 214273-22-0
• 化学式: C₁₆H₂₂O₂Si
• 分子量: 274.435
• InChiKey: OZAXTPRIUUPCRJ-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.29
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-5-benzyloxy-4-methyl-1-trimethylsilylpent-1-yn-3-one 在 (4R)-2-甲基-4,5,5-三苯基-1,3,2-恶唑硼烷 、 dimethyl sulfide borane 、 bis(cyclohexanyl)borane 作用下， 以 四氢呋喃 为溶剂， 生成 (3S,4S)-5-benzyloxy-3-hydroxy-4-methylpentanoic 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：

  Weinreb amide of (S)-3-benzyloxy-2-methylpropionic acid 、 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 3.5h， 以90%的产率得到(S)-5-benzyloxy-4-methyl-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

文献信息

• Stereoselective reduction of α′-branched α,β-ynones. Application to the synthesis of the Octalactin A ring
  作者：Jordi Bach、Jordi Garcia

  DOI：10.1016/s0040-4039(98)01420-8

  日期：1998.9

  A flexible, efficient route to chiral 3-hydroxy-4-methyl- and 3-hydroxy-4-methoxyalkanoic acids, with high control of the C(3) configuration, has been disclosed, which is based on the borane-mediated reduction of 1-trimethylsilyl-1-alkyn-3-ones (6) in the presence of oxazaborolidine 7 followed by hydroboration of the resulting propargylic alcohols 4 and 5. This strategy has been applied to the synthesis of the Octalactin A ring. (C) 1998 Elsevier Science Ltd. All rights reserved.
• A Synthetic Approach to 3-Hydroxy 4-Substituted Carboxylic Acids based on the Stereoselective Reduction of 1-Trimethylsilyl-1-alkyn-3-ones
  作者：Carme Alemany、Jordi Bach、Jordi Garcia、Marta López、Ana B. Rodrı́guez

  DOI：10.1016/s0040-4020(00)00905-4

  日期：2000.11

  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.