(1R,4R,E)-1-((S)-4-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-5-((4-methoxybenzyl)oxy)-4-methylpent-2-en-1-ol | 1344072-92-9

• 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: (1R,4R,E)-1-((S)-4-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-5-((4-methoxybenzyl)oxy)-4-methylpent-2-en-1-ol
• CAS: 1344072-92-9
• 化学式: C₂₀H₃₀O₆
• 分子量: 366.455
• InChiKey: HKHRDQOEVUSUPI-GLLNCQHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  26.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  77.38
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1R,4R,E)-1-((S)-4-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-5-((4-methoxybenzyl)oxy)-4-methylpent-2-en-1-ol 、 2,2-二甲氧基丙烷 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以2 mg的产率得到(5R,6R)-6-[(E,3R)-4-[(4-methoxyphenyl)methoxy]-3-methylbut-1-enyl]-2,2,8,8-tetramethyl-1,3,7,9-tetraoxaspiro[4.5]decane
  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
• 作为产物：
  描述：

  2,2,2-三氯代亚氨逐乙酸-4-甲氧基苄酯 在 N-(p-toluenesulfonyl)-L-valine 、 manganese(IV) oxide 、 硼烷四氢呋喃络合物 、 草酰氯 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 sodium hydride 、 二异丁基氢化铝 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 、 mineral oil 为溶剂， 反应 22.5h， 生成 (1R,4R,E)-1-((S)-4-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-5-((4-methoxybenzyl)oxy)-4-methylpent-2-en-1-ol
  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