methyl (R)-3-(tert-butyldimethylsilyloxy)octadecanoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (R)-3-(tert-butyldimethylsilyloxy)octadecanoate
• 英文别名: methyl (3R)-3-[tert-butyl(dimethyl)silyl]oxyoctadecanoate
• 化学式: C₂₅H₅₂O₃Si
• 分子量: 428.772
• InChiKey: BZTIMOYVRCJAAR-HSZRJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.42
• 重原子数：
  29
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (R)-3-(tert-butyldimethylsilyloxy)octadecanoate 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 (3R)-3-[tert-butyl(dimethyl)silyl]oxyoctadecanal
  参考文献：
  名称：

  Sphinganine和Clavaminol H的不对称合成

  摘要：

  报道了一种有效的对映体选择性合成斯潘加宁和卡瓦米酚H的方法。这些鞘氨醇型碱是通过使用高度对映选择性的Ru催化的氢化反应和有机催化的亲电胺化反应从立体异构中心获得的，可从市售脂肪酸中获得。

  DOI：

  10.1021/jo1003899
• 作为产物：
  描述：

  (R)-3-hydroxyoctadecanoic acid 在 吡啶 、 4-二甲氨基吡啶 、 三氟化硼 作用下， 反应 72.33h， 生成 methyl (R)-3-(tert-butyldimethylsilyloxy)octadecanoate
  参考文献：
  名称：

  Properties of unusual phospholipids. III: Synthesis, monolayer investigations and DSC studies of hydroxy octadeca(e)noic acids and diacylglycerophosphocholines derived therefrom

  摘要：

  Diacylglycerophosphocholines containing (R)-3-, (R)-12-, (R)-17-hydroxy octadeca(e)noic acids and the corresponding racemates were synthesized and purified to homogeneity. The influence of the position of the hydroxy group on the monolayer packing properties of these fatty acids and their phosphatidylcholines was studied by Langmuir techniques and 1,2-di-[(R)-12-hydroxy-octadec-cis-9-enyl]-sn-glycero-3-phosphocholine displayed the largest lift-off area (330 Angstrom(2)/molecule). This result was in line with the thermotropic phase behavior of these phospholipids, as measured by differential scanning calorimetry (DSC): the gel-to liquid-crystalline phase transition temperature (T-m) passed through a minimum of -15.1 degrees C for 1,2-di-[(R)-12-hydroxy-octadec-cis-9-enyl]-sn-glycero-3-phosphocholine. (C) 1997 Elsevier Science Ireland Ltd.

  DOI：

  10.1016/s0009-3084(97)00085-6

文献信息

• Asymmetric Synthesis of Sphinganine and Clavaminol H
  作者：Ramzi Ait-Youcef、Xavier Moreau、Christine Greck

  DOI：10.1021/jo1003899

  日期：2010.8.6

  An efficient enantioselective synthesis of sphinganine and clavaminol H is reported. These sphingoid-type bases were obtained from commercially available fatty acids using highly enantioselective Ru-catalyzed hydrogenation and organocatalytic electrophilic amination reactions to create the stereogenic centers.

  报道了一种有效的对映体选择性合成斯潘加宁和卡瓦米酚H的方法。这些鞘氨醇型碱是通过使用高度对映选择性的Ru催化的氢化反应和有机催化的亲电胺化反应从立体异构中心获得的，可从市售脂肪酸中获得。
• Properties of unusual phospholipids. III: Synthesis, monolayer investigations and DSC studies of hydroxy octadeca(e)noic acids and diacylglycerophosphocholines derived therefrom
  作者：Lars Negelmann、Sandra Pisch、Uwe Bornscheuer、Rolf D Schmid

  DOI：10.1016/s0009-3084(97)00085-6

  日期：1997.11

  Diacylglycerophosphocholines containing (R)-3-, (R)-12-, (R)-17-hydroxy octadeca(e)noic acids and the corresponding racemates were synthesized and purified to homogeneity. The influence of the position of the hydroxy group on the monolayer packing properties of these fatty acids and their phosphatidylcholines was studied by Langmuir techniques and 1,2-di-[(R)-12-hydroxy-octadec-cis-9-enyl]-sn-glycero-3-phosphocholine displayed the largest lift-off area (330 Angstrom(2)/molecule). This result was in line with the thermotropic phase behavior of these phospholipids, as measured by differential scanning calorimetry (DSC): the gel-to liquid-crystalline phase transition temperature (T-m) passed through a minimum of -15.1 degrees C for 1,2-di-[(R)-12-hydroxy-octadec-cis-9-enyl]-sn-glycero-3-phosphocholine. (C) 1997 Elsevier Science Ireland Ltd.