4-((E)-1-((tert-butyldimethylsilyl)oxy)-3-phenylallyl)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde | 1344073-01-3

• 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: 4-((E)-1-((tert-butyldimethylsilyl)oxy)-3-phenylallyl)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde
• 英文别名: (4S)-4-[(E,1R)-1-[tert-butyl(dimethyl)silyl]oxy-3-phenylprop-2-enyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde
• CAS: 1344073-01-3
• 化学式: C₂₁H₃₂O₄Si
• 分子量: 376.568
• InChiKey: NGPQMYHNVUYIDG-FXIHAIIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 N-(p-toluenesulfonyl)-L-valine 、 硼烷四氢呋喃络合物 、 sodium hexamethyldisilazane 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 二氯甲烷 为溶剂， 反应 2.17h， 生成 4-((E)-1-((tert-butyldimethylsilyl)oxy)-3-phenylallyl)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde 、 (R)-4-((S,E)-1-((tert-butyldimethylsilyl)oxy)-3-phenylallyl)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde 、 4-((E)-1-((tert-butyldimethylsilyl)oxy)-3-phenylallyl)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde
  参考文献：
  名称：

  A Kiyooka Aldol Approach for the Synthesis of the C(14)–C(23) Segment of the Diastereomeric Analog of Tedanolide C

  摘要：

  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.

  DOI：

  10.1021/ol202515x

文献信息

• Concise Asymmetric Synthesis of Kweichowenol A
  作者：David Konrad、Bilal Kicin、Dirk Trauner

  DOI：10.1055/s-0037-1610390

  日期：2019.3

  An asymmetric 11-step synthesis of the polyoxygenated cyclohexene natural product kweichowenol A from the traditional Chinese medicinal herb Uvaria kweichowesis is reported. The oxygenation pattern was installed on a linear precursor by exploiting the acyclic stereocontrol of the Kiyooka aldol reaction, as well as Cram chelate-controlled Grignard reactions. Ring-closing metathesis and a selective benzoylation

  报道了一种不对称 11 步合成来自传统中草药 Uvaria kweichowesis 的多氧化环己烯天然产物 kweichowenol A。通过利用清冈醛醇反应的无环立体控制以及克拉姆螯合物控制的格氏反应，将氧化模式安装在线性前体上。然后闭环复分解和选择性苯甲酰化得到天然产物。