1-O-(Z)-octadecenyl-2-O-methyl-sn-glycerol | 150949-19-2

• 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-O-(Z)-octadecenyl-2-O-methyl-sn-glycerol
• 英文别名: 3-O-(cis-9-octadecenyl)-2-O-methyl-sn-glycerol
• CAS: 150949-19-2
• 化学式: C₂₂H₄₄O₃
• 分子量: 356.59
• InChiKey: YDUAAOKPSVKGJO-GMAFFVFYSA-N

物化性质

• 沸点：
  456.6±35.0 °C(predicted)
• 密度：
  0.900±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.05
• 重原子数：
  25.0
• 可旋转键数：
  20.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-O-(Z)-octadecenyl-2-O-methyl-sn-glycerol 在 三氟甲磺酸三甲基硅酯 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 21.0h， 生成 3-O-(cis-9-octadecenyl)-2-O-methyl-sn-glycero-1-phosphocholine
  参考文献：
  名称：

  Synthesis of enantiomerically pure ether lipid analogues from d-mannitol

  摘要：

  A new scheme for synthesis of enantiomerically pure ether lipid analogues 3-O-octadecyl-2-O-methyl-sn-glycero-phosphocholine (D-ET-18-OCH3), 1-O-octadecyl-2-O-methyl-sn-glycero-phosphocholine (L-ET-18-OCH3) and their oleyl analogues is described. The key steps are regioselective reductive cleavage of 2,5-di-O-methyl-1,3:4,6-bis-O-(40-methoxybenzylidene)-D-mannitol (I) either with NaBH3CN-Me3SiCl (Br) giving 2,5-di-O-methyl-3,4-bis-O-(4-methoxybenzyl)-D-mannitol (II) or with NaBH3CN-CF3COOH to afford 2,5-di-O-methyl-1,6-bis-O-(4-methoxybenzyl)-D-mannitol (III). Compounds (II) and (III) are chiral precursors for synthesis of ether phospholipids of L- and D-series, respectively. The procedure described proved to be applicable to the preparation of ether lipids having also the unsaturated alkyl chains. The enantiomeric excess of obtained 1- and/or 3-alkyl-2-O-methyl-sn-glycerols was about 98%, as confirmed by H-1-NMR using chiral shift reagent, Eu(hfc)3. This synthetic strategy makes possible the preparation of the enantiomers of 1- and/or 3-O-alkyl-2-O-methyl-sn-glycerophosphocholines in good yield and high optical purity from the same starting material, 2,5-di-O-methyl-1,3:4,6-bis-O-(4-methoxybenzylidene)-D-mannitol (1), without the use of additional protective groups.

  DOI：

  10.1016/0009-3084(93)90082-e
• 作为产物：
  描述：

  1-O-(4-methoxybenzyl)-2-O-methyl-3-O-(cis-9-octadecenyl)-sn-glycerol 在 ammonium cerium(IV) nitrate 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 1.5h， 以89%的产率得到1-O-(Z)-octadecenyl-2-O-methyl-sn-glycerol
  参考文献：
  名称：

  Synthesis of enantiomerically pure ether lipid analogues from d-mannitol

  摘要：

  A new scheme for synthesis of enantiomerically pure ether lipid analogues 3-O-octadecyl-2-O-methyl-sn-glycero-phosphocholine (D-ET-18-OCH3), 1-O-octadecyl-2-O-methyl-sn-glycero-phosphocholine (L-ET-18-OCH3) and their oleyl analogues is described. The key steps are regioselective reductive cleavage of 2,5-di-O-methyl-1,3:4,6-bis-O-(40-methoxybenzylidene)-D-mannitol (I) either with NaBH3CN-Me3SiCl (Br) giving 2,5-di-O-methyl-3,4-bis-O-(4-methoxybenzyl)-D-mannitol (II) or with NaBH3CN-CF3COOH to afford 2,5-di-O-methyl-1,6-bis-O-(4-methoxybenzyl)-D-mannitol (III). Compounds (II) and (III) are chiral precursors for synthesis of ether phospholipids of L- and D-series, respectively. The procedure described proved to be applicable to the preparation of ether lipids having also the unsaturated alkyl chains. The enantiomeric excess of obtained 1- and/or 3-alkyl-2-O-methyl-sn-glycerols was about 98%, as confirmed by H-1-NMR using chiral shift reagent, Eu(hfc)3. This synthetic strategy makes possible the preparation of the enantiomers of 1- and/or 3-O-alkyl-2-O-methyl-sn-glycerophosphocholines in good yield and high optical purity from the same starting material, 2,5-di-O-methyl-1,3:4,6-bis-O-(4-methoxybenzylidene)-D-mannitol (1), without the use of additional protective groups.

  DOI：

  10.1016/0009-3084(93)90082-e