1-(allyloxy)-3-(tert-butyldiphenylsilyloxy)propan-2-ol | 595605-41-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 1-(allyloxy)-3-(tert-butyldiphenylsilyloxy)propan-2-ol
• 英文别名: 1-allyl-3-tert-butyldiphenylsilyl-rac-glycerol；1-[Tert-butyl(diphenyl)silyl]oxy-3-prop-2-enoxypropan-2-ol
• CAS: 595605-41-7
• 化学式: C₂₂H₃₀O₃Si
• 分子量: 370.564
• InChiKey: FBVZCRRGODMUOU-UHFFFAOYSA-N

物化性质

• 沸点：
  441.0±45.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  26
• 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：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(allyloxy)-3-(tert-butyldiphenylsilyloxy)propan-2-ol 在 咪唑 、 四丁基氟化铵 、 仲丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 3.25h， 生成 1-O-(1'-(Z)-hexadecenyl)-2-(2-trimethylsilanylethoxymethyl)-rac-glycerol
  参考文献：
  名称：

  Direct Synthesis of Plasmenylcholine from Allyl-Substituted Glycerols

  摘要：

  We report a new method for the facile preparation of plasmenylcholine via reaction of lithioalkoxy allyl intermediates with 1-iodoalkanes as the key step in the stereoselective formation of 1'-(Z)-alkenyl glyceryl ethers. The allyl anion intermediate is prepared by treating mono- or disiloxyprotected 1-allylglycerol precursors with s-BuLi at -65 to -80degreesC. Subsequent addition of 1-iodoalkane solutions at low temperature gives moderate yields of gamma-coupled, Z-vinyl ethers as the major product and alpha-coupled product as the minor component. Several different preparative strategies for the total synthesis of plasmalogens are enabled by this simple transformation.

  DOI：

  10.1021/jo026826w
• 作为产物：
  描述：

  4-烯丙基氧基甲基-2,2-二甲基-1,3-二氧杂环戊烷 在 咪唑 、 盐酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 1-(allyloxy)-3-(tert-butyldiphenylsilyloxy)propan-2-ol
  参考文献：
  名称：

  [EN] SUBSTITUTED PYRIDONE COMPOUNDS USEFUL TO TREAT ORTHOMYXOVIRUS INFECTIONS
  [FR] COMPOSÉS DE PYRIDONE SUBSTITUÉS UTILES POUR TRAITER DES INFECTIONS À ORTHOMYXOVIRUS

  摘要：

  The disclosure provides compounds of Formula (I): (I) as further described herein, as well as pharmaceutical compositions comprising such compounds, and methods to use the compounds and pharmaceutical compositions for treatment of certain viral disorders, including influenza.

  公开号：

  WO2023002443A1

文献信息

• Monoallylation of 1,2-Diols by Pd/Sn Bimetallic Catalysis
  作者：Masami Kuriyama、Tsubasa Takeichi、Masaaki Ito、Noritsugu Yamasaki、Ryota Yamamura、Yosuke Demizu、Osamu Onomura

  DOI：10.1002/chem.201102709

  日期：2012.2.27

  Efficient and mild: The selective monoallylation of 1,2‐diols was successfully developed with Pd/Sn bimetallic catalysis in good to excellent yields. This process was carried out with high substrate tolerance under mild conditions (see scheme). The catalyst system achieved the quite high chemoselectivity even in the presence of a 1:1 mixture of the 1,2‐diol and mono‐ol.

  高效且温和：通过Pd / Sn双金属催化成功地开发了1,2-二醇的选择性单烯丙基化，收率良好至极佳。该过程在温和条件下以较高的基材耐受性进行（参见方案）。即使存在1,2-二醇和一元醇的1：1混合物，该催化剂体系也实现了很高的化学选择性。
• Direct Synthesis of Plasmenylcholine from Allyl-Substituted Glycerols
  作者：Junhwa Shin、David H. Thompson

  DOI：10.1021/jo026826w

  日期：2003.8.1

  We report a new method for the facile preparation of plasmenylcholine via reaction of lithioalkoxy allyl intermediates with 1-iodoalkanes as the key step in the stereoselective formation of 1'-(Z)-alkenyl glyceryl ethers. The allyl anion intermediate is prepared by treating mono- or disiloxyprotected 1-allylglycerol precursors with s-BuLi at -65 to -80degreesC. Subsequent addition of 1-iodoalkane solutions at low temperature gives moderate yields of gamma-coupled, Z-vinyl ethers as the major product and alpha-coupled product as the minor component. Several different preparative strategies for the total synthesis of plasmalogens are enabled by this simple transformation.
• [EN] SUBSTITUTED PYRIDONE COMPOUNDS USEFUL TO TREAT ORTHOMYXOVIRUS INFECTIONS<br/>[FR] COMPOSÉS DE PYRIDONE SUBSTITUÉS UTILES POUR TRAITER DES INFECTIONS À ORTHOMYXOVIRUS
  申请人：[en]NOVARTIS AG

  公开号：WO2023002443A1

  公开（公告）日：2023-01-26

  The disclosure provides compounds of Formula (I): (I) as further described herein, as well as pharmaceutical compositions comprising such compounds, and methods to use the compounds and pharmaceutical compositions for treatment of certain viral disorders, including influenza.