(2R,3S,4S,5S,6R)-2-(dodecylamino)-6-(hydroxymethyl)oxane-3,4,5-triol | 174391-42-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4S,5S,6R)-2-(dodecylamino)-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 174391-42-5
• 化学式: C₁₈H₃₇NO₅
• 分子量: 347.495
• InChiKey: CGRNGAJCQIWCRM-DFBDCSAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  102
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethoxycarbonyl octadecanoate 、 (2R,3S,4S,5S,6R)-2-(dodecylamino)-6-(hydroxymethyl)oxane-3,4,5-triol 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以79%的产率得到N-dodecyl-N-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]octadecanamide
  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：

  十二烷基伯胺 、 beta-D-吡喃甘露糖 以 乙醇 为溶剂， 反应 0.25h， 以88%的产率得到(2R,3S,4S,5S,6R)-2-(dodecylamino)-6-(hydroxymethyl)oxane-3,4,5-triol
  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

文献信息

• N-glycosylierte Harnstoffe, Carbamate und Thiocarbamate, Verfahren zu ihrer Herstellung sowie ihre Verwendung
  申请人：BAYER AG

  公开号：EP0149093A2

  公开（公告）日：1985-07-24

  Die vorliegende Erfindung betrifft neue N-glycosylierte Harnstoffe, Carbamate und Thiocarbamate der allgemeinen Formel I in welcher R1, R2, X und Z die in der Beschreibung angegebene Bedeutung besitzen, Verfahren zu ihrer Herstellung sowie ihre Verwendung zur Beeinflussung der körpereigenen Abwehr.

  本发明涉及通式 I（其中 R1、R2、X 和 Z 具有说明中给出的含义）的新型 N-糖基化脲类、氨基甲酸酯类和硫代氨基甲酸酯类化合物，涉及它们的制备工艺和用于影响人体自身防御的用途。
• US4737488A
  申请人：——

  公开号：US4737488A

  公开（公告）日：1988-04-12
• Syntheses of glycosylamides as glycolipid analogs
  作者：Oswald Lockhoff、Peter Stadler

  DOI：10.1016/s0008-6215(98)00278-x

  日期：1998.12

  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.