N-((2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-tetradecylamino-tetrahydro-pyran-3-yl)-acetamide | 223384-95-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-((2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-tetradecylamino-tetrahydro-pyran-3-yl)-acetamide
• CAS: 223384-95-0
• 化学式: C₂₂H₄₄N₂O₅
• 分子量: 416.602
• InChiKey: SNFZKVAZKWZGAX-ZGJYDULXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.22
• 重原子数：
  29.0
• 可旋转键数：
  16.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  111.05
• 氢给体数：
  5.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Ethoxycarbonyl octadecanoate 、 N-((2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-tetradecylamino-tetrahydro-pyran-3-yl)-acetamide 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以72%的产率得到Octadecanoic acid ((2R,3R,4R,5S,6R)-3-acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-tetradecyl-amide
  参考文献：
  名称：

  Syntheses of glycosylamides as glycolipid analogs

  摘要：

  In search of a simple synthetic access to analogs of naturally occurring glycolipids, glycosylamides have been synthesised in a two-step procedure from unprotected sugars, long-chain amines, and fatty acids. The N-glycosylation proceeded stereospecifically yielding crystalline beta-glycopyranosylamines. C-13 NMR spectroscopy of the glycosylamines in organic solvents revealed partial anomerisation, leading to alpha-glycosylamines and in part to corresponding N-furanosides. Selective N-acylation of either pure beta-glycosylamines or anomeric mixtures thereof with activated fatty acid led to formation of beta-glycosylamides exclusively. As evidenced by NMR spectroscopy, the glycosylamides exhibited rotameric isomerism. The glycosylamides were found to be strong stimulators of the specific immune response against antigens. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00278-x
• 作为产物：
  描述：

  2-乙酰氨基-2-脱氧-beta-D-吡喃葡萄糖胺 、 十四胺 以 乙醇 为溶剂， 反应 0.25h， 以69%的产率得到N-((2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-tetradecylamino-tetrahydro-pyran-3-yl)-acetamide
  参考文献：
  名称：

  Syntheses of glycosylamides as glycolipid analogs

  摘要：

  In search of a simple synthetic access to analogs of naturally occurring glycolipids, glycosylamides have been synthesised in a two-step procedure from unprotected sugars, long-chain amines, and fatty acids. The N-glycosylation proceeded stereospecifically yielding crystalline beta-glycopyranosylamines. C-13 NMR spectroscopy of the glycosylamines in organic solvents revealed partial anomerisation, leading to alpha-glycosylamines and in part to corresponding N-furanosides. Selective N-acylation of either pure beta-glycosylamines or anomeric mixtures thereof with activated fatty acid led to formation of beta-glycosylamides exclusively. As evidenced by NMR spectroscopy, the glycosylamides exhibited rotameric isomerism. The glycosylamides were found to be strong stimulators of the specific immune response against antigens. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00278-x