(2S,4R,5S)-4-bromo-2-(tert-butyldimethylsilyloxy)-5-hydroxy-6-methyl-3-heptanone | 1189128-33-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4R,5S)-4-bromo-2-(tert-butyldimethylsilyloxy)-5-hydroxy-6-methyl-3-heptanone
• 英文别名: (2S,4R,5S)-4-bromo-2-[tert-butyl(dimethyl)silyl]oxy-5-hydroxy-6-methylheptan-3-one
• CAS: 1189128-33-3
• 化学式: C₁₄H₂₉BrO₃Si
• 分子量: 353.372
• InChiKey: DFVLHYZFDIFAMV-TUAOUCFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,4R,5S)-4-bromo-2-(tert-butyldimethylsilyloxy)-5-hydroxy-6-methyl-3-heptanone 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以84%的产率得到(2S,4S,5S)-4-azido-2-(tert-butyldimethylsilyloxy)-5-hydroxy-6-methyl-3-heptanone
  参考文献：
  名称：

  Stereoselective Synthesis of Highly Functionalized Structures from Lactate-Derived Halo Ketones

  摘要：

  Highly diastereoselective (i-PrO)(2)TiCl2-mediated aldol reactions from lactate-derived alpha'-halo alpha-silyloxy ketones and subsequent treatment of the resultant aldols with a wide range of nucleophiles furnishes highly functionalized arrangements useful in natural product syntheses.

  DOI：

  10.1021/jo9010798
• 作为产物：
  描述：

  (S) 1-bromo-3-(tert-butyldimethylsilyloxy)-2-butanone 、 异丁醛 在 titanium(IV) isopropylate 、 四氯化钛 、 N,N-二异丙基乙胺 、 氯化铵 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以69%的产率得到(2S,4R,5S)-4-bromo-2-(tert-butyldimethylsilyloxy)-5-hydroxy-6-methyl-3-heptanone
  参考文献：
  名称：

  Stereoselective Synthesis of Highly Functionalized Structures from Lactate-Derived Halo Ketones

  摘要：

  Highly diastereoselective (i-PrO)(2)TiCl2-mediated aldol reactions from lactate-derived alpha'-halo alpha-silyloxy ketones and subsequent treatment of the resultant aldols with a wide range of nucleophiles furnishes highly functionalized arrangements useful in natural product syntheses.

  DOI：

  10.1021/jo9010798

文献信息

• Stereoselective Synthesis of Highly Functionalized Structures from Lactate-Derived Halo Ketones
  作者：Joaquim Nebot、Pedro Romea、Fèlix Urpí

  DOI：10.1021/jo9010798

  日期：2009.10.2

  Highly diastereoselective (i-PrO)(2)TiCl2-mediated aldol reactions from lactate-derived alpha'-halo alpha-silyloxy ketones and subsequent treatment of the resultant aldols with a wide range of nucleophiles furnishes highly functionalized arrangements useful in natural product syntheses.