(S)-1-O-linolenoyl-2-O-palmitoyl-sn-glycerol

• 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: (S)-1-O-linolenoyl-2-O-palmitoyl-sn-glycerol
• 英文别名: DG(18:3(9Z,12Z,15Z)/16:0/0:0)；[(2S)-2-hexadecanoyloxy-3-hydroxypropyl] (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
• 化学式: C₃₇H₆₆O₅
• 分子量: 590.928
• InChiKey: RSSYCPWLZRHABI-DSZXWZEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.8
• 重原子数：
  42
• 可旋转键数：
  33
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-1-O-linolenoyl-2-O-palmitoyl-sn-glycerol 、 甲氧基-三氟甲基苯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以92%的产率得到
  参考文献：
  名称：

  Synthesis of polyunsaturated fatty acid-containing glucuronosyl-diacylglycerol through direct glycosylation

  摘要：

  We describe a total synthesis of a polyunsaturated fatty acid (PUFA)-containing glucuronosyl-diacylglycerol (G1cADG), which is a surrogate glycolipid whose synthesis is remarkably upregulated in plant membranes under phosphorus-depleted conditions. Glycosylation between the glucuronide donor bearing 3,4-dimethoxybenzyl (DMPM) protecting groups and di-acylglycerol acceptor proceeded smoothly in the presence of gold(I) catalyst to provide the protected alpha-isomer of G1cADG as the major product. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2017.06.034
• 作为产物：
  描述：

  Γ-十八碳三烯酸 在 吡啶 、 (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylaminomorpholinocarbenium hexafluorophosphate 、 氟化氢吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 36.66h， 生成 (S)-1-O-linolenoyl-2-O-palmitoyl-sn-glycerol
  参考文献：
  名称：

  Synthesis of polyunsaturated fatty acid-containing glucuronosyl-diacylglycerol through direct glycosylation

  摘要：

  We describe a total synthesis of a polyunsaturated fatty acid (PUFA)-containing glucuronosyl-diacylglycerol (G1cADG), which is a surrogate glycolipid whose synthesis is remarkably upregulated in plant membranes under phosphorus-depleted conditions. Glycosylation between the glucuronide donor bearing 3,4-dimethoxybenzyl (DMPM) protecting groups and di-acylglycerol acceptor proceeded smoothly in the presence of gold(I) catalyst to provide the protected alpha-isomer of G1cADG as the major product. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2017.06.034

文献信息

• Synthesis of polyunsaturated fatty acid-containing glucuronosyl-diacylglycerol through direct glycosylation
  作者：Qianqian Wang、Yuta Kuramoto、Yozo Okazaki、Eisuke Ota、Masaki Morita、Go Hirai、Kazuki Saito、Mikiko Sodeoka

  DOI：10.1016/j.tetlet.2017.06.034

  日期：2017.7

  We describe a total synthesis of a polyunsaturated fatty acid (PUFA)-containing glucuronosyl-diacylglycerol (G1cADG), which is a surrogate glycolipid whose synthesis is remarkably upregulated in plant membranes under phosphorus-depleted conditions. Glycosylation between the glucuronide donor bearing 3,4-dimethoxybenzyl (DMPM) protecting groups and di-acylglycerol acceptor proceeded smoothly in the presence of gold(I) catalyst to provide the protected alpha-isomer of G1cADG as the major product. (C) 2017 Elsevier Ltd. All rights reserved.