(N-tetradecanoyl-2-aminoethyl) 4-O-(β-D-galactopyranosyl)-β-D-glucopyranoside

• 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: (N-tetradecanoyl-2-aminoethyl) 4-O-(β-D-galactopyranosyl)-β-D-glucopyranoside
• 英文别名: N-[2-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyethyl]tetradecanamide
• 化学式: C₂₈H₅₃NO₁₂
• 分子量: 595.728
• InChiKey: INSUBSNJGJKFME-QFOURGAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  41
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  208
• 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 palladium on activated charcoal 吡啶 、 sodium azide 、 三氟化硼乙醚 、 氢气 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 65.0h， 生成 (N-tetradecanoyl-2-aminoethyl) 4-O-(β-D-galactopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  An Improved Synthetic Procedure for the Preparation of N‐Acyl (2‐aminoethyl)‐β‐d‐glycopyranoside Lipids and Characterization of Their Mesogenic Properties

  摘要：

  A modified synthetic procedure was used for the synthesis of N-acyl (2-aminoethyl) glycosides bearing lactose, maltose, and melibiose carbohydrate headgroups and different acyl chains. The lipid glycosides were prepared in gram scale and investigated for their liquid crystalline properties. It was found that the polar spacer suppresses polymorphism, and the resulting simplified phase behavior was found in the pure state upon heating, as well as for the lyotropic phases.

  DOI：

  10.1080/07328300601082385

文献信息

• An Improved Synthetic Procedure for the Preparation of <i>N</i>‐Acyl (2‐aminoethyl)‐β‐<scp>d</scp>‐glycopyranoside Lipids and Characterization of Their Mesogenic Properties
  作者：Götz Milkereit、Volkmar Vill

  DOI：10.1080/07328300601082385

  日期：2006.12.1

  A modified synthetic procedure was used for the synthesis of N-acyl (2-aminoethyl) glycosides bearing lactose, maltose, and melibiose carbohydrate headgroups and different acyl chains. The lipid glycosides were prepared in gram scale and investigated for their liquid crystalline properties. It was found that the polar spacer suppresses polymorphism, and the resulting simplified phase behavior was found in the pure state upon heating, as well as for the lyotropic phases.