(2R,3R,4S,5R,6R)-2-(dodecylamino)-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol | 223384-84-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5R,6R)-2-(dodecylamino)-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
• 英文别名: (2R,3R,4S,5R,6R)-2-(dodecylamino)-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 223384-84-7
• 化学式: C₁₈H₃₇NO₅
• 分子量: 347.495
• InChiKey: CGRNGAJCQIWCRM-DISONHOPSA-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,3R,4S,5R,6R)-2-(dodecylamino)-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以69%的产率得到N-dodecyl-N-[(2R,3R,4S,5R,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 、 β-半乳糖苷酶 以 乙醇 为溶剂， 反应 6.0h， 以77%的产率得到(2R,3R,4S,5R,6R)-2-(dodecylamino)-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
  参考文献：
  名称：

  Influence of the Variation of the Alkyl Chain Length ofN-Alkyl-β-d-glycosylamine Derivatives on Antifungal Properties

  摘要：

  Twelve new glucosidic and galactosidic derivatives of N-alkylaminosugars with different alkylamines from 6 to 18 carbons were synthesized and characterized by H-1 and C-13 NMR. Their antifungal activity against the food fungal pathogen Aspergillus niger was evaluated using the radial growth assay. The influence of the variation of the alkyl chain length of N-alkylaminosugars on the mycelium growth was then discussed. Inhibition by the different alkylamines is shown as a biostatic effect rather than a biocidal effect. It was observed that alkylamines keep their antifungal properties after a thermal treatment compatible with food packaging and processing.

  DOI：

  10.1021/jf3015798

文献信息

• Efficient synthesis of glycosylamines in solventless conditions promoted by mechanical milling
  作者：Cédric Epoune Lingome、Gwladys Pourceau、Virginie Gobert-Deveaux、Anne Wadouachi

  DOI：10.1039/c4ra04321a

  日期：——

  A mecanosynthesis of glycosylamines under solventless conditions was established. This environmentally friendly approach optimized with L-rhamnose, was investigated using a variety of amines and other carbohydrates. High reaction yields and simple work-up allow the clean and fast synthesis of a variety of glycosylamines and glycosyl-(di)-amines.

  建立了在无溶剂条件下糖基胺的机械合成。使用多种胺类和其他碳水化合物对这种以L-鼠李糖优化的环保方法进行了研究。高反应产率和简单的后处理使得各种糖基胺和糖基-（二）-胺的清洁和快速合成成为可能。
• NOVEL METHOD FOR SYNTHESIZING N-ALKYL-GLYCOSYL(DI)AMINE DERIVATIVES AND USES OF SAME AGAINST PHYTOPATHOGENS
  申请人：UNIVERSITE DE PICARDIE JULES VERNE

  公开号：US20160102115A1

  公开（公告）日：2016-04-14

  The present invention relates to a novel method for synthesising, without a solvent, N-alkyl-glycosyl(di)amine derivatives represented by the following general formula (I): The invention also concerns the use of N-alkyl-glycosyl(di)amine derivatives represented by the general formula (I), and N-alkyl-glycosyl(di)ammonium quaternary salts represented by the general formula (II) and N-alkyl-glycamine derivatives represented by the general formula (III) obtained from N-alkyl-glycosyl(di)amine derivatives represented by the general formula (I), as antibacterial and/or antifungal agents against phytopathogens.

  本发明涉及一种新型方法，用于合成以下一般式(I)所代表的无溶剂N-烷基-糖基（二）胺衍生物。本发明还涉及使用由一般式(I)所代表的N-烷基-糖基（二）胺衍生物、一般式(II)所代表的N-烷基-糖基（二）胺盐和由一般式(I)所代表的N-烷基-糖基（二）胺衍生物所得到的一般式(III)所代表的N-烷基-糖胺衍生物作为抗菌和/或抗真菌剂，用于对抗植物病原体。
• Phosphorylierte Glycosylamide, -harnstoffe, -carbamate und -thiocarbamate, Verfahren zu ihrer Herstellung sowie ihre Verwendung
  申请人：BAYER AG

  公开号：EP0143385A2

  公开（公告）日：1985-06-05

  Die Erfindung betrifft Verbindungen der allgemeinen Formel Verfahren zu ihrer Herstellung und ihre Verwendung bei der Bekämpfung von Krankheiten.

  本发明涉及通式化合物的制备工艺及其在防治疾病中的应用。
• Substituierte O-Acyl-Glycosylamide, Verfahren zu ihrer Herstellung sowie ihre Verwendung
  申请人：BAYER AG

  公开号：EP0149760B1

  公开（公告）日：1989-08-23
• Substituierte O-Sulfonyl-Glycosylamide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel
  申请人：BAYER AG

  公开号：EP0193887B1

  公开（公告）日：1989-07-26