(E,1R,4R)-1-[(4S)-4-[[tert-butyl(dimethyl)silyl]oxy-methoxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-5-[(4-methoxyphenyl)methoxy]-4-methylpent-2-en-1-ol | 1344072-77-0

• 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: (E,1R,4R)-1-[(4S)-4-[[tert-butyl(dimethyl)silyl]oxy-methoxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-5-[(4-methoxyphenyl)methoxy]-4-methylpent-2-en-1-ol
• CAS: 1344072-77-0
• 化学式: C₂₇H₄₆O₇Si
• 分子量: 510.744
• InChiKey: ZYVYKRBEIAQEPV-WVIMQZMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.28
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (2R)-3-[(4-methoxybenzyl)oxy]-2-methylpropanol 在 N-(p-toluenesulfonyl)-L-valine 、 manganese(IV) oxide 、 硼烷四氢呋喃络合物 、 草酰氯 、 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 1.67h， 生成 (E,1R,4R)-1-[(4S)-4-[[tert-butyl(dimethyl)silyl]oxy-methoxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-5-[(4-methoxyphenyl)methoxy]-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

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.