(E,2R)-2-Methyl-5-(tert-butyldimethylsiloxy)pent-3-en-1-ol | 121012-21-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (E,2R)-2-Methyl-5-(tert-butyldimethylsiloxy)pent-3-en-1-ol
• 英文别名: (E,2R)-5-[tert-butyl(dimethyl)silyl]oxy-2-methylpent-3-en-1-ol
• CAS: 121012-21-3
• 化学式: C₁₂H₂₆O₂Si
• 分子量: 230.423
• InChiKey: FVUKBJGGYMRLQU-WSKFYRRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E,2R)-2-Methyl-5-(tert-butyldimethylsiloxy)pent-3-en-1-ol 在 氢氟酸 、 sodium hydride 作用下， 以 丙酮 为溶剂， 反应 6.0h， 生成 (2E,4R)-5-(benzyloxy)-4-methyl-2-penten-1-ol
  参考文献：
  名称：

  Very high chemoselective, regioselective, and E-stereoselective 1,3-chirality transfer involving reaction of acyclic (E)- and (Z)-.gamma.-mesyloxy .alpha.,.beta.-enoates and organocyanocopper-trifluoroborane reagents. Efficient synthetic routes to functionalized chiral .alpha.-alkyl (E)-.beta.,.gamma.-enoates and (E)-allylic alcohols with high optical purity

  摘要：

  DOI：

  10.1021/ja00195a045
• 作为产物：
  描述：

  (E)-(R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-pent-3-enoic acid ethyl ester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以91%的产率得到(E,2R)-2-Methyl-5-(tert-butyldimethylsiloxy)pent-3-en-1-ol
  参考文献：
  名称：

  Very high chemoselective, regioselective, and E-stereoselective 1,3-chirality transfer involving reaction of acyclic (E)- and (Z)-.gamma.-mesyloxy .alpha.,.beta.-enoates and organocyanocopper-trifluoroborane reagents. Efficient synthetic routes to functionalized chiral .alpha.-alkyl (E)-.beta.,.gamma.-enoates and (E)-allylic alcohols with high optical purity

  摘要：

  DOI：

  10.1021/ja00195a045

文献信息

• A Kiyooka Aldol Approach for the Synthesis of the C(14)–C(23) Segment of the Diastereomeric Analog of Tedanolide C
  作者：Leila Bülow、Arun Naini、Jörg Fohrer、Markus Kalesse

  DOI：10.1021/ol202515x

  日期：2011.11.18

  The challenging synthesis of a quaternary center within the highly oxygenated setting of tedanolide C can be performed via a Kiyooka aldol reaction. Here, the diastereomeric analog of tedanolide C with the configurations between C10 and C20 opposite compared to the proposed structure was chosen as the synthetic target. The tetra-substituted silyl ketene acetal provides the southern hemisphere of tedanolide C in useful selectivities, and the absolute configuration of the newly generated quaternary center was determined by NOE experiments of the corresponding acetonide.