2-undecyl-5-β-lactosyl-1,4,5,6-tetrahydropyrimidine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-undecyl-5-β-lactosyl-1,4,5,6-tetrahydropyrimidine
• 英文别名: (2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2-undecyl-1,4,5,6-tetrahydropyrimidin-5-yl)oxy]oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₂₇H₅₀N₂O₁₁
• 分子量: 578.701
• InChiKey: KSFQYJLPFOKJOU-UAHSQCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  40
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  203
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 在 sodium azide 、 三氟化硼乙醚 、 sodium methylate 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 2-undecyl-5-β-lactosyl-1,4,5,6-tetrahydropyrimidine
  参考文献：
  名称：

  N-linked glycolipids by Staudinger coupling of glycosylated alkyl diazides with fatty acids

  摘要：

  Aiming for new glycolipids with enhanced chemical stability and close structural similarity to natural cell membrane lipids for the development of a drug delivery system, we have synthesized double amide analogs of glyco-glycerolipids. The synthesis applied a Staudinger reaction based coupling of a 1,3-diazide with fatty acid chlorides. While the concept furnished the desired glucosides in reasonable yields, the corresponding lactosides formed a tetrahydropyrimidine based 1: 1 coupling product instead. This unexpected coupling result likely originates from steric hindrance at the iminophosphorane intermediate and provides an interesting core structure for potentially bioactive surfactants. The assembly behavior of both glycolipid types was investigated by optical polarizing microscopy, DSC and surface tension studies. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.03.028

文献信息

• N-linked glycolipids by Staudinger coupling of glycosylated alkyl diazides with fatty acids
  作者：Salih Mahdi Salman、Thorsten Heidelberg、Hairul Anuar Bin Tajuddin

  DOI：10.1016/j.carres.2013.03.028

  日期：2013.6

  Aiming for new glycolipids with enhanced chemical stability and close structural similarity to natural cell membrane lipids for the development of a drug delivery system, we have synthesized double amide analogs of glyco-glycerolipids. The synthesis applied a Staudinger reaction based coupling of a 1,3-diazide with fatty acid chlorides. While the concept furnished the desired glucosides in reasonable yields, the corresponding lactosides formed a tetrahydropyrimidine based 1: 1 coupling product instead. This unexpected coupling result likely originates from steric hindrance at the iminophosphorane intermediate and provides an interesting core structure for potentially bioactive surfactants. The assembly behavior of both glycolipid types was investigated by optical polarizing microscopy, DSC and surface tension studies. (C) 2013 Elsevier Ltd. All rights reserved.