(S,2E,4E)-6-(((tert-Butyldiphenylsilyl)oxy)methyl)octa-2,4-dien-1-ol | 1321530-47-5

• 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: (S,2E,4E)-6-(((tert-Butyldiphenylsilyl)oxy)methyl)octa-2,4-dien-1-ol
• 英文别名: (2E,4E,6S)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]octa-2,4-dien-1-ol
• CAS: 1321530-47-5
• 化学式: C₂₅H₃₄O₂Si
• 分子量: 394.629
• InChiKey: QANLUHRVCMUGSS-COUNKINGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  、 (E)-3-(tri-n-butylstannyl)-2-propen-1-ol 在 双(乙腈)氯化钯(II) 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 1.5h， 生成 、 (S,2E,4E)-6-(((tert-Butyldiphenylsilyl)oxy)methyl)octa-2,4-dien-1-ol
  参考文献：
  名称：

  Catalytic Enantioselective Total Synthesis of (+)-Torrubiellone C

  摘要：

  Silyl-protected (R)-methyl 2-(hydroxymethyl)butanoate was obtained by an enantioselective Ir-catalyzed hydrogenation In high yield and selectivity. Elaboration of this building block via Takai and Stille reactions gave a protected hydroxy polyene chain, which was coupled to a 5-hydroxyphenyl-4-hydroxy-2-pyridone derivative by a modified Horner-Wadsworth-Emmons reaction. Deprotection gave synthetic (+)-torrublelione C, which led to the assignment of the configuration of the natural product as (R).

  DOI：

  10.1021/ol201692h

文献信息

• Catalytic Enantioselective Total Synthesis of (+)-Torrubiellone C
  作者：Henning J. Jessen、Andreas Schumacher、Fabian Schmid、Andreas Pfaltz、Karl Gademann

  DOI：10.1021/ol201692h

  日期：2011.8.19

  Silyl-protected (R)-methyl 2-(hydroxymethyl)butanoate was obtained by an enantioselective Ir-catalyzed hydrogenation In high yield and selectivity. Elaboration of this building block via Takai and Stille reactions gave a protected hydroxy polyene chain, which was coupled to a 5-hydroxyphenyl-4-hydroxy-2-pyridone derivative by a modified Horner-Wadsworth-Emmons reaction. Deprotection gave synthetic (+)-torrublelione C, which led to the assignment of the configuration of the natural product as (R).