2-O-allyl-D-glyceraldehyde dimethylacetal | 166102-95-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-O-allyl-D-glyceraldehyde dimethylacetal
• CAS: 166102-95-0
• 化学式: C₈H₁₆O₄
• 分子量: 176.213
• InChiKey: WXOCBWWJPRYLCU-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.17
• 重原子数：
  12.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-O-allyl-D-glyceraldehyde dimethylacetal 在 盐酸 、 四丁基碘化铵 、 sodium hydride 作用下， 反应 25.25h， 生成 2-O-allyl-3-O-benzyl-D-glyceraldehyde
  参考文献：
  名称：

  New optically pure dimethylacetals of glyceraldehydes and their application for lipid and phospholipid synthesis

  摘要：

  A convenient synthesis of new and enantiomerically pure 2-O-protected D-glyceraldehyde dimethylacetals as chiral C-3 building blocks for the synthesis of lipids and phospholipids is described. Benzyl- or allylethers are used as protecting groups in position 2 and 5 of D-mannitol. These intermediates are converted to 2-O-benzyl- or 2-O-allyl-D-glyceraldehyde dimethylacetals by cleavage with periodic acid in methanol. The two dimethylacetals are useful for the synthesis of mixed chain phospholipids with natural configuration of ester-ester, ester-ether or ether-ether composition. Also, triglycerides with three different alkyl chains, ester or ether, can be prepared. As an example of the versatility of the new intermediates, we describe the synthesis of 1-O-hexahecyl-2-O-acetyl-sn-glycero-3-phosphocholine, the so-called 'platelet activating factor' (PAF), via 1-O-hexadecyl-2-O-benzyl-sn-glycerol.

  DOI：

  10.1016/0009-3084(95)02445-o
• 作为产物：
  描述：

  甲醇 、 1,3:4,6-di-O-benzylidene-2,5-di-O-allyl-D-mannitol 在 硫酸 、 过碘酸 作用下， 反应 6.0h， 以72%的产率得到2-O-allyl-D-glyceraldehyde dimethylacetal
  参考文献：
  名称：

  New optically pure dimethylacetals of glyceraldehydes and their application for lipid and phospholipid synthesis

  摘要：

  A convenient synthesis of new and enantiomerically pure 2-O-protected D-glyceraldehyde dimethylacetals as chiral C-3 building blocks for the synthesis of lipids and phospholipids is described. Benzyl- or allylethers are used as protecting groups in position 2 and 5 of D-mannitol. These intermediates are converted to 2-O-benzyl- or 2-O-allyl-D-glyceraldehyde dimethylacetals by cleavage with periodic acid in methanol. The two dimethylacetals are useful for the synthesis of mixed chain phospholipids with natural configuration of ester-ester, ester-ether or ether-ether composition. Also, triglycerides with three different alkyl chains, ester or ether, can be prepared. As an example of the versatility of the new intermediates, we describe the synthesis of 1-O-hexahecyl-2-O-acetyl-sn-glycero-3-phosphocholine, the so-called 'platelet activating factor' (PAF), via 1-O-hexadecyl-2-O-benzyl-sn-glycerol.

  DOI：

  10.1016/0009-3084(95)02445-o