(2R,3S)-2-methyl-3-(t-butyldimethylsilyloxy)-5-phenylpentanal | 1227673-16-6

• 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: (2R,3S)-2-methyl-3-(t-butyldimethylsilyloxy)-5-phenylpentanal
• 英文别名: (2R,3S)-3-[tert-butyl(dimethyl)silyl]oxy-2-methyl-5-phenylpentanal
• CAS: 1227673-16-6
• 化学式: C₁₈H₃₀O₂Si
• 分子量: 306.521
• InChiKey: ORJQTPXOUBCZAT-RDJZCZTQSA-N

物化性质

• 沸点：
  371.4±42.0 °C(predicted)
• 密度：
  0.935±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.84
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 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：

  (2R,3S)-2-methyl-3-(t-butyldimethylsilyloxy)-5-phenylpentanal 、 (R,R)-1,3-二-(4-溴苄基)-2-氯八氢-2-(2Z)-巴豆基-1H-1,3,2-苯并二氮杂硅杂环戊烷 在 scandium tris(trifluoromethanesulfonate) 、 tetra-n-butylammoniumfluoride trihydrate 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 以74%的产率得到(3R,4S,5S,6S)-6-[tert-butyl(dimethyl)silyl]oxy-3,5-dimethyl-8-phenyloct-1-en-4-ol
  参考文献：
  名称：

  A More Comprehensive and Highly Practical Solution to Enantioselective Aldehyde Crotylation

  摘要：

  The enantioselective crotylation of aldehydes with 1,2-diaminochlorocrotylsilane reagents is effectively catalyzed by Sc(OTf)(3). The one significant limitation on the utility of these reagents - substrate scope - has thus been addressed. The net result is the most comprehensive and highly practical method for enantioselective aldehyde crotylation yet advanced.

  DOI：

  10.1021/ja200712f

文献信息

• Catalytic Asymmetric Synthesis of Complex Polypropionates: Lewis Base Catalyzed Aldol Equivalents in the Synthesis of Erythronolide B
  作者：Binita Chandra、Dezhi Fu、Scott G. Nelson

  DOI：10.1002/anie.200906245

  日期：2010.3.29

  Powerful aldol reactions: Stereoselective Lewis base catalyzed aldol equivalents expediently provided eight of the ten stereocenters required for the synthesis of erythronolide B. Indeed, all eleven stereocenters present in the erythromycin aglycone have been derived directly or indirectly from catalytic asymmetric equivalents of aldol addition reactions (see scheme).

  强大的羟醛反应：立体选择性路易斯碱催化的羟醛等效物可提供合成赤藓醇内酯B所需的十个立体中心中的八个。参见方案）。
• A More Comprehensive and Highly Practical Solution to Enantioselective Aldehyde Crotylation
  作者：Hyunwoo Kim、Stephen Ho、James L. Leighton

  DOI：10.1021/ja200712f

  日期：2011.5.4

  The enantioselective crotylation of aldehydes with 1,2-diaminochlorocrotylsilane reagents is effectively catalyzed by Sc(OTf)(3). The one significant limitation on the utility of these reagents - substrate scope - has thus been addressed. The net result is the most comprehensive and highly practical method for enantioselective aldehyde crotylation yet advanced.