(2S,4R,5S)-2-tert-butyldimethylsilyloxy-5-hydroxy-4,7-dimethyl-3-octanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4R,5S)-2-tert-butyldimethylsilyloxy-5-hydroxy-4,7-dimethyl-3-octanone
• 英文别名: (2S,4R,5S)-2-[tert-butyl(dimethyl)silyl]oxy-5-hydroxy-4,7-dimethyloctan-3-one
• 化学式: C₁₆H₃₄O₃Si
• 分子量: 302.53
• InChiKey: DKYASZBJIKSYEK-RDBSUJKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (S)-2-(tert-butyldimethylsilanyloxy)-N-methoxy-N-methylpropionamide 在 四氯化钛 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 (2S,4R,5S)-2-tert-butyldimethylsilyloxy-5-hydroxy-4,7-dimethyl-3-octanone
  参考文献：
  名称：

  Stereoselective titanium-mediated aldol reactions of (S)-2-tert-butyldimethylsilyloxy-3-pentanone

  摘要：

  Titanium-mediated aldol reactions based on (S)-2-tert-butyldimethylsilyloxy-3-pentanone, a lactate-derived chiral ketone, provide the corresponding 2,4-syn-4,5-syn adducts in high yields and diastereomeric ratios with a wide array of achiral and chiral aldehydes. Furthermore, spectroscopic studies of intermediates involved in the process have permitted to propose a mechanism that accounts for the experimental results. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.034

文献信息

• Enolization of Chiral α-Silyloxy Ketones with Dicyclohexylchloroborane. Application to Stereoselective Aldol Reactions
  作者：Marta Galobardes、Miguel Gascón、Marisa Mena、Pedro Romea、Fèlix Urpí、Jaume Vilarrasa

  DOI：10.1021/ol006109t

  日期：2000.8.1

  [reaction: see text]Comprehensive analysis of the enolization of alpha-silyloxyketones by Chx2BCl/R3N has allowed us to design stereoselective Chx2BCl-mediated aldol processes that afford syn or anti aldol products and to disclose a hypothesis that accounts for the subtle effects that determine their enolization.

  [反应：参见文本] Chx2BCl / R3N对α-甲硅烷基氧酮烯醇化的全面分析，使我们能够设计立体选择性Chx2BCl介导的羟醛工艺，该工艺提供顺式或反式羟醛产物，并揭示一种假说，该假说解释了确定他们的烯醇化。
• Stereoselective titanium-mediated aldol reactions of (S)-2-tert-butyldimethylsilyloxy-3-pentanone
  作者：Joaquim Nebot、Sergi Figueras、Pedro Romea、Fèlix Urpí、Yining Ji

  DOI：10.1016/j.tet.2006.09.034

  日期：2006.11

  Titanium-mediated aldol reactions based on (S)-2-tert-butyldimethylsilyloxy-3-pentanone, a lactate-derived chiral ketone, provide the corresponding 2,4-syn-4,5-syn adducts in high yields and diastereomeric ratios with a wide array of achiral and chiral aldehydes. Furthermore, spectroscopic studies of intermediates involved in the process have permitted to propose a mechanism that accounts for the experimental results. (c) 2006 Elsevier Ltd. All rights reserved.