1,6-di-O-octadecyl-2,5-di-O-methyl-D-mannitol | 90126-20-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,6-di-O-octadecyl-2,5-di-O-methyl-D-mannitol
• 英文别名: 1,6-dioctadecyl-2,5-dimethyl-D-mannitol；(2R,3S,4S,5R)-2,5-dimethoxy-1,6-dioctadecoxyhexane-3,4-diol
• CAS: 90126-20-8
• 化学式: C₄₄H₉₀O₆
• 分子量: 715.195
• InChiKey: WCJCYJRKDNXMNU-OWIHLRRYSA-N

物化性质

• 沸点：
  735.4±60.0 °C(Predicted)
• 密度：
  0.920±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  16.2
• 重原子数：
  50
• 可旋转键数：
  43
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,6-di-O-octadecyl-2,5-di-O-methyl-D-mannitol 在 sodium tetrahydroborate 、 sodium periodate 作用下， 生成 (2S)-2-甲氧基-3-(十八烷氧基)-1-丙醇
  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：

  十八烷基甲烷磺酸酯 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 乙醇 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 生成 1,6-di-O-octadecyl-2,5-di-O-methyl-D-mannitol
  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

文献信息

• EIBL, H.
  作者：EIBL, H.

  DOI：——

  日期：——
• NEUE D-MANNIT-ABKÖMMLINGE ALS VORPRODUKTE ZUR SYNTHESE VON PHOSPHOLIPIDEN
  申请人：Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.

  公开号：EP0116566B1

  公开（公告）日：1988-06-08
• US4734225A
  申请人：——

  公开号：US4734225A

  公开（公告）日：1988-03-29
• US4804789A
  申请人：——

  公开号：US4804789A

  公开（公告）日：1989-02-14
• Synthesis of enantiomerically pure ether lipid analogues from d-mannitol
  作者：Anatoly N. Pinchuk、Boris I. Mitsner、Vitaly I. Shvets

  DOI：10.1016/0009-3084(93)90082-e

  日期：1993.4

  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.