N-octadecyl-β-D-glucopyranosylamine | 3676-76-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-octadecyl-β-D-glucopyranosylamine
• 英文别名: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(octadecylamino)tetrahydropyran-3,4,5-triol；(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(octadecylamino)oxane-3,4,5-triol
• CAS: 3676-76-4
• 化学式: C₂₄H₄₉NO₅
• 分子量: 431.657
• InChiKey: HDZVAKYKVBEOFL-GNADVCDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  30
• 可旋转键数：
  19
• 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：

  N-octadecyl-β-D-glucopyranosylamine 、 Ethoxycarbonyl octadecanoate 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以78%的产率得到N-octadecyl-N-[(2R,3R,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：

  可得然胶 、 十八胺 以 甲醇 为溶剂， 以96%的产率得到N-octadecyl-β-D-glucopyranosylamine
  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

• N-glycosylated carboxamide derivatives as growth-promoters in livestock
  申请人：Bayer Aktiengesellschaft

  公开号：US04680287A1

  公开（公告）日：1987-07-14

  Growth of animals is promoted by inclusion in their feed of compounds of the formula ##STR1## in which Z is a glycosyl radical bonded via the anomeric carbon atom, R.sub.1 is hydrogen or an optionally substituted hydrocarbon radical having up to 30 Carbon atoms optionally interrupted by O, N or S, and R.sub.2 is hydrogen or an alkyl or aralkyl radical having up to 30 Carbon atoms optionally interrupted by O or substituted by groups containing oxygen or by halogen, with the proviso that COR.sub.1 is not an acyl group having 1-5 Carbon atoms when R.sub.2 is an alkyl group having 10-20 Carbon atoms.

  动物生长可以通过在其饲料中添加以下化合物的形式得到促进：其中Z是通过异头碳原子连接的糖基自由基，R1是氢或者是一个最多含有30个碳原子，可以选择性地被O、N或S原子隔断的，也可以选择性地被取代的烃基团，而R2是氢或者是一个最多含有30个碳原子的烷基或芳烷基团，可以选择性地被O原子隔断或被含氧基团或卤素取代，条件是当R2是一个含有10-20个碳原子的烷基团时，COR1不能是一个含有1-5个碳原子的酰基团。
• N-glycosylated carboxamide derivatives and their use for influencing the
  申请人：Bayer Aktiengesellschaft

  公开号：US04683222A1

  公开（公告）日：1987-07-28

  The invention relates to N-glycosylated carboxamide derivatives of Formula I which are useful for influencing the body's inherent defenses, e.g. for increasing immune system antibodies. Also included in the invention are compositions containing said N-glycosylated carboxamide derivative of Formula I as active ingredients and methods for the use of said compounds and compositions.

  本发明涉及式I的N-糖基化羧酰胺衍生物，它们可用于影响机体的固有防御，例如用于增加免疫系统的抗体。发明还包括含有式I的N-糖基化羧酰胺衍生物作为活性成分的组合物，以及使用所述化合物和组合物的方法。
• N-glycosylated carboxylic acid derivatives as agents for combating
  申请人：Troponwerke GmbH & Co., KG

  公开号：US04710491A1

  公开（公告）日：1987-12-01

  A method of combating rheumatic diseases which comprises administering to a patient afflicted therewith an amount effective to combat such disease of a compound of the formula ##STR1## in which Z is a glycosyl radical bonded via the anomeric carbon atom, R.sub.1 is hydrogen or an optionally substituted hydrocarbon radical with up to 30 C atoms, which hydrocarbon radical is optionally interrupted by O, N or S, and R.sub.2 is hydrogen or an alkyl or aralkyl radical with up to 30 C atoms, which is optionally interrupted by O, N or S or substituted by an oxygen-containing group or halogen, with the proviso that COR.sub.1 is not an acyl group with 1-5 C atoms if R.sub.2 is alkyl with 10-20 C atoms.

  一种治疗风湿病的方法，包括给患者施用有效治疗该疾病的量的以下化合物的公式：##STR1## 其中Z是通过异构碳原子连接的糖基自由基，R1是氢或最多有30个碳原子的可选取代的烃基，该烃基可被O、N或S隔断，R2是氢或最多有30个碳原子的烷基或芳烷基，该基团可被O、N或S隔断或被含氧基团或卤素取代，条件是如果R2是10-20个碳原子的烷基，则COR1不是1-5个碳原子的酰基。
• Substituted O-sulphonyl-glycosylamides, processes for their preparation
  申请人：Bayer Aktiengesellschaft

  公开号：US04699899A1

  公开（公告）日：1987-10-13

  Novel compounds of the formula ##STR1## in which X is hydrogen or --CH.sub.2 --OR.sup.5, Z represents OR.sup.4, NH.sub.2 or ##STR2## R.sup.2, R.sup.3, R.sup.4 and R.sup.5 each independently is hydrogen or ##STR3## at least one of R.sup.2, R.sup.3, R.sup.4 and R.sup.5 being ##STR4## Y and W each independently is oxygen, sulphur, NH or CH.sub.2, and R.sup.1, R.sup.6, R.sup.7 and R.sup.8 each independently is an optionally substituted hydrocarbon radical with up to 50 C atoms, stimulate the immune system.

  该文描述了式子##STR1##中的新化合物，其中X为氢或--CH.sub.2 --OR.sup.5，Z代表OR.sup.4，NH.sub.2或##STR2##，R.sup.2、R.sup.3、R.sup.4和R.sup.5各自独立地是氢或##STR3##，其中至少一个是##STR4##，Y和W各自独立地是氧、硫、NH或CH.sub.2，而R.sup.1、R.sup.6、R.sup.7和R.sup.8各自独立地是具有最多50个碳原子的可选取代的碳氢基团，可刺激免疫系统。
• Substituted O-acylglycosylamides, pharmaceutical compositions and method
  申请人：Bayer Aktiengesellschaft

  公开号：US04574122A1

  公开（公告）日：1986-03-04

  Compounds of the formula ##STR1## in which X is hydrogen or the radical --CH.sub.2 OR.sup.5, three of R.sup.2, R.sup.3, R.sup.4 and R.sup.5 each independently is hydrogen or ##STR2## and the fourth is ##STR3## Z each independently is oxygen, sulphur, NH or CH.sub.2, and R.sup.1, R.sup.6 and R.sup.7 each independently is an optionally substituted hydrocarbon radical having up to 50 carbon atoms, stimulate the immune system's response and antibody production.

  分子式为##STR1##的化合物，其中X为氢或基团--CH.sub.2 OR.sup.5，R.sup.2、R.sup.3、R.sup.4和R.sup.5中的三个分别独立地为氢或##STR2##，第四个为##STR3##，Z独立地为氧、硫、NH或CH.sub.2，R.sup.1、R.sup.6和R.sup.7各自独立地为具有最多50个碳原子的可选取代的碳氢基团，可刺激免疫系统的反应和抗体产生。