((2S)-1-O-linolenoyl-3-O-β-D-galactopyranosyl-sn-glycerol) | 420840-09-1

• 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: ((2S)-1-O-linolenoyl-3-O-β-D-galactopyranosyl-sn-glycerol)
• 英文别名: panaxcerol B；SF391；3-alpha-linolenoylglycerol 1-O-beta-d-galactopyranoside；[2-hydroxy-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropyl] (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
• CAS: 420840-09-1
• 化学式: C₂₇H₄₆O₉
• 分子量: 514.657
• InChiKey: HUSISCNTLUEZCN-FZAXDPBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  36
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  146
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  3-O-(β-D-2',3',4',6'-tetra-O-acetyl-galactopyranosyl)-rac-glycerol 在 4-二甲氨基吡啶 、 水 、 一水合肼 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 ((2S)-1-O-linolenoyl-3-O-β-D-galactopyranosyl-sn-glycerol)
  参考文献：
  名称：

  An efficient and versatile chemical synthesis of bioactive glyco-glycerolipids

  摘要：

  Synthesis of beta-glyco-1,2-diacylglycerols is achieved by a versatile and simple procedure based on trichloro-acetimidate methodology and use of peracetate sugar substrates. The chemical strategy was tested through stereoselective preparation of beta-galacto- and beta-gluco-lipid derivatives capable to trigger immune system response. The synthetic approach is designed to obtain enantiomerically pure regio- and stereo-isomers including derivatives containing poly-unsaturated fatty acids. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.12.030

文献信息

• An efficient and versatile chemical synthesis of bioactive glyco-glycerolipids
  作者：Emiliano Manzo、Maria Letizia Ciavatta、Dario Pagano、Angelo Fontana

  DOI：10.1016/j.tetlet.2011.12.030

  日期：2012.2

  Synthesis of beta-glyco-1,2-diacylglycerols is achieved by a versatile and simple procedure based on trichloro-acetimidate methodology and use of peracetate sugar substrates. The chemical strategy was tested through stereoselective preparation of beta-galacto- and beta-gluco-lipid derivatives capable to trigger immune system response. The synthetic approach is designed to obtain enantiomerically pure regio- and stereo-isomers including derivatives containing poly-unsaturated fatty acids. (C) 2011 Elsevier Ltd. All rights reserved.