2-O-methoxyethoxymethylglycerol | 93135-78-5

• 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: 2-O-methoxyethoxymethylglycerol
• 英文别名: 1,3-Propanediol, 2-[(2-methoxyethoxy)methoxy]-；2-(2-methoxyethoxymethoxy)propane-1,3-diol
• CAS: 93135-78-5
• 化学式: C₇H₁₆O₅
• 分子量: 180.201
• InChiKey: KETIWGVHGWQRSK-UHFFFAOYSA-N

物化性质

• 沸点：
  292.8±30.0 °C(Predicted)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  12
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-O-methoxyethoxymethylglycerol 在 吡啶 、 三乙胺 、 三氯氧磷 作用下， 反应 21.5h， 生成 rac-1-O-cis,cis-9,12-octadecadienyl-2-O-<(methoxyethoxy)methyl>glycero-3-phosphocholine
  参考文献：
  名称：

  Facile synthesis of platelet-activating factor and racemic analogs containing unsaturation in the sn-1-alkyl chain

  摘要：

  Platelet-activating factor, 1 (PAF, 1-O-hexadecyl-2-acetyl-sn-glycero-3-phosphocholine), and octadecyl-PAF were synthesized chemically as the racemates. The sn-1-O-alkyl isomers were isolated after treatment of the racemates with phospholipase A2 and subsequent reacetylation of the 1-O-alkyl-2-lyso-sn-glycero-3-phosphocholines released. Analogues of PAF containing unsaturated alkyl moieties at the sn-1 position (2, 4, 5) were synthesized by utilizing the methoxyethoxymethyl protecting group as a novel method for preparing unsaturated alkyl lipids. This procedure provides a facile means for preparing unsaturated either phospholipids of defined structure that may be tritiated to high radiospecific activity for metabolic studies. Unsaturation in the alkyl chain had minimal effect on the bioactivities examined in this study.

  DOI：

  10.1021/jm00379a015
• 作为产物：
  描述：

  2-O-<(methoxyethoxy)methyl>-1,3-benzylideneglycerol 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 2-O-methoxyethoxymethylglycerol
  参考文献：
  名称：

  Facile synthesis of platelet-activating factor and racemic analogs containing unsaturation in the sn-1-alkyl chain

  摘要：

  Platelet-activating factor, 1 (PAF, 1-O-hexadecyl-2-acetyl-sn-glycero-3-phosphocholine), and octadecyl-PAF were synthesized chemically as the racemates. The sn-1-O-alkyl isomers were isolated after treatment of the racemates with phospholipase A2 and subsequent reacetylation of the 1-O-alkyl-2-lyso-sn-glycero-3-phosphocholines released. Analogues of PAF containing unsaturated alkyl moieties at the sn-1 position (2, 4, 5) were synthesized by utilizing the methoxyethoxymethyl protecting group as a novel method for preparing unsaturated alkyl lipids. This procedure provides a facile means for preparing unsaturated either phospholipids of defined structure that may be tritiated to high radiospecific activity for metabolic studies. Unsaturation in the alkyl chain had minimal effect on the bioactivities examined in this study.

  DOI：

  10.1021/jm00379a015

文献信息

• Synthesis of Phosphatidylcholine Having a Very Long Chain Polyunsaturated Fatty Acid
  作者：Syed Shabbir Haider、Masatoshi Tanaka、Md Khorshed Alam、Shuhei Nakajima、Naomichi Baba、Sakayu Shimizu

  DOI：10.1246/cl.1998.175

  日期：1998.2

  groups at the 1- and 2-positions respectively was synthesized. The synthetic route involves carbon chain elongation of linoleic acid via malonic ester synthesis, preparation of lyso-phosphatidylcholine via lipase-catalyzed mon-acylation of 2-O-methoxyethoxymethylglycerol and phosphodiester synthesis, and finally DCC-mediated esterification.

  合成了分别在 1-和 2-位带有二十碳二烯酰基和二十二碳六烯酰基的磷脂酰胆碱 9。合成路线包括通过丙二酸酯合成亚油酸的碳链延长，通过脂肪酶催化的 2-O-甲氧基乙氧基甲基甘油单酰化和磷酸二酯合成制备溶血磷脂酰胆碱，最后是 DCC 介导的酯化。
• Baba, Naomichi; Akiyama, Takeshi; Tahara, Shoichi, Bioscience, Biotechnology and Biochemistry, 1995, vol. 59, # 2, p. 353 - 354
  作者：Baba, Naomichi、Akiyama, Takeshi、Tahara, Shoichi、Nakajima, Shuhei

  DOI：——

  日期：——
• Facile synthesis of platelet-activating factor and racemic analogs containing unsaturation in the sn-1-alkyl chain
  作者：Jefferson R. Surles、Robert L. Wykle、Joseph T. O'Flaherty、William L. Salzer、Michael J. Thomas、Fred Snyder、Claude Piantadosi

  DOI：10.1021/jm00379a015

  日期：1985.1

  Platelet-activating factor, 1 (PAF, 1-O-hexadecyl-2-acetyl-sn-glycero-3-phosphocholine), and octadecyl-PAF were synthesized chemically as the racemates. The sn-1-O-alkyl isomers were isolated after treatment of the racemates with phospholipase A2 and subsequent reacetylation of the 1-O-alkyl-2-lyso-sn-glycero-3-phosphocholines released. Analogues of PAF containing unsaturated alkyl moieties at the sn-1 position (2, 4, 5) were synthesized by utilizing the methoxyethoxymethyl protecting group as a novel method for preparing unsaturated alkyl lipids. This procedure provides a facile means for preparing unsaturated either phospholipids of defined structure that may be tritiated to high radiospecific activity for metabolic studies. Unsaturation in the alkyl chain had minimal effect on the bioactivities examined in this study.