N-butyl-β-D-glucopyranosylamine | 3679-04-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-butyl-β-D-glucopyranosylamine
• 英文别名: (2R,3R,4S,5S,6R)-2-(butylamino)-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 3679-04-7
• 化学式: C₁₀H₂₁NO₅
• 分子量: 235.28
• InChiKey: DEJYGEBDYDDFRP-HOTMZDKISA-N

物化性质

• 熔点：
  97-98 °C
• 沸点：
  427.7±45.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  16
• 可旋转键数：
  5
• 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-butyl-β-D-glucopyranosylamine 在 重水 作用下， 反应 168.0h， 生成
  参考文献：
  名称：

  Synthesis ofN-Alkyl-β-d-glucosylamines and Their Antimicrobial Activity againstFusarium proliferatum,Salmonellatyphimurium, andListeria innocua

  摘要：

  In this study, different N-alkyl-beta-D-glucosylamines were evaluated for both antifungal and antibacterial activity against Fusarium proliferatum (INRA, MUCL 1807.7), Listeria innocua (ISTAB, Universite Bordeaux 1), and Salmonella typhimurium (Institut Pasteur 5858). The tested glucosylamines were beta-D-glucosylamine (GPA), N-ethyl-beta-D-glucosylamine (EtGPA), N-butyl-beta-D-glucosylamine (BuGPA), N-hexyl-beta-D-glucosylamine (HeGPA), N-octyl-beta-D-glucosylamine (OcGPA), N-dodecyl-beta-D-glucosylamine (DoGPA), N-(2-hydroxyethyl)-beta-D-glucosylamine (HEtGPA), N,N-di(2-hydroxyethyl)-beta-D-glucosylamine (DHEtGPA) and N,N-diethyl-beta-D-glucosylamine (DEtGPA). The effectiveness of N-alkyl length, N-substitution, and N-hydroxyalkyl groups on both antibacterial and antifungal activity were evaluated. Results indicated that these compounds exhibited different biological activities and their effectiveness was highly increased from short to long N-alkyl chains. DoGPA exhibited more potent biological activity against all target strains than other N-alkyl glucosylamines tested. Using a radial growth method, we demonstrated that this compound completely inhibited fungal growth at 0.5 x 10(-4) mol mL(-1), while OcGPA and HeGPA lead to 71% and 43% fungal inhibition, respectively. Using the coating method, we demonstrated that DoGPA completely inhibited bacterial growth at 0.025 x 10(-4) and 0.05 x 10(-4) mol mL(-1) for L. innocua and S. typhimurium, respectively, while at the same concentrations, OcGPA exhibited weaker antibacterial activity of 12% and 27%, respectively, for L. innocua and S. typhimurium. The hole plate method enabled us to estimate the minimum inhibitory concentration (MIC) of DoGPA found to be 0.02 x 10(-4) and 0.025 x 10(-4) mol mL(-1) for L. innocua and S. typhimurium, respectively. Glucosylamines with N-hydroxyalkyl and short N-alkyl chains varying from C-2 to C-4 exhibited weaker antimicrobial activity.

  DOI：

  10.1021/jf9016114
• 作为产物：
  描述：

  可得然胶 、 正丁胺 以 乙醇 为溶剂， 反应 4.5h， 以79%的产率得到N-butyl-β-D-glucopyranosylamine
  参考文献：
  名称：

  1 : 1 Adduct Ion Formation of Simple Carbohydrate Derivatives with Cations Using FAB Mass Spectrometry. Comparison ofO-Acetyl,N-Butyl, andO-Methyl Modifications

  摘要：

  使用 FAB 质谱法定量检测了一系列过-O-乙酰化醛吡喃糖（1 族）或 N-丁酰化糖基胺（2 族）与有机/金属阳离子（n-C8H17NH3+/K+ 或 Li+）之间形成的 1 : 1 加合物离子。过-O-乙酰基修饰显著降低了碳水化合物对阳离子的选择性，这一点在过-O-甲基修饰中也得到了清晰的观察。另一方面，单-N-丁基修饰提供了与单-O-甲基修饰相似的选择性模式。根据电子和结构方面的考虑，我们可以理解这些结果。

  DOI：

  10.1246/bcsj.65.1275

文献信息

• <i>N</i>-glycosylation approach to glucose-functionalized diamine and its use for protection-free synthesis of polyurea bearing glucoside pendant
  作者：Atsushi Sudo、Shou Sugita

  DOI：10.1002/pola.26376

  日期：2013.1.15

  glucose‐functionalized diamine was prepared and used as a new monomer for polyurea synthesis. The diamine was prepared by N‐glycosylation of 1,6‐hexamethylenediamine with D‐glucose. Upon adding diisocyanates to the diamine, isocyanate reacted selectively with the amino groups, not with the hydroxyl groups of the glucose‐derived structure, to give the corresponding polyureas. The polyureas exhibited highly

  制备了葡萄糖官能化的二胺，并将其用作聚脲合成的新单体。二胺是通过D-葡萄糖对1,6-六亚甲基二胺进行N-糖基化制得的。向二胺中添加二异氰酸酯后，异氰酸酯会与氨基（而不是与葡萄糖衍生结构的羟基）发生选择性反应，生成相应的聚脲。由于存在葡萄糖衍生的侧链，因此聚脲表现出高度亲水性。由葡萄糖官能化的二胺，哌嗪和二异氰酸酯组成的三元体系产生相应的聚脲，其中葡萄糖衍生部分的含量可通过二胺和哌嗪之间的进料比进行调节。©2012 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem，2013年
• 一种无保护糖合成N-糖苷的方法
  申请人：中国药科大学

  公开号：CN117567525A

  公开（公告）日：2024-02-20

  本发明涉及化学合成技术领域，更具体的说是涉及一种无保护糖合成N‑糖苷的方法，其特征在于，在温度为‑78℃～25℃条件下，将无保护的糖基给体、受体和碱溶于水或者水和有机溶剂的混合溶剂中，加入促进剂，反应获得相应的糖苷，本发明合成了一系列DMC的类似物，该类似物无文献报道，属于新化合物，其可以介导受体为碱基的无保护糖糖苷化，同时也可以特异性结合受体的9位N。该方法避免了上下保护基的复杂操作，糖苷化反应的产物立体选择性高，大大降低了糖苷化合成操作的复杂性和合成成本。
• Synthesis and evaluation of N-alkyl-β-d-glucosylamines on the growth of two wood fungi, Coriolus versicolor and Poria placenta
  作者：Théoneste Muhizi、Véronique Coma、Stéphane Grelier

  DOI：10.1016/j.carres.2008.07.005

  日期：2008.9

  Various glucosylamines were synthesized from glucose and different alkyl amine compounds. These amino compounds are P-D-glucopyranosylamine (GPA), N-ethyl-beta-D-glucopyranosylamine (EtGPA), N-butyl-beta-D-glucopyranosylamine (BuGPA), N-hexyl-beta-D-glucopyranosylamine (HeGPA), N-octyl-beta-D-glucopyranosylamine (OcGPA), N-dodecyl-beta-D-glucopyranosylamine (DoGPA), N-(2-hydroxyethyl)-beta-D-glucopyranosylamine (HEtGPA) and N,N-di(2-hydroxyethyl)-beta-D-glucopyranosylamine (DHEtGPA). They were tested for their antifungal activity against the growth of Coriolus versicolor and Poria placenta. An improvement of the antifungal activity with the increase of alkyl chain length was observed. DoGPA exhibited the best antifungal activity against both strains. It completely inhibited the fungal growth at 0.01 x 10(-3) mol mL(-1) and 0.0075 x 10-3 Mol mL(-1) for C. versicolor and P. placenta, respectively. For other glucosylamines higher concentrations were needed for complete inhibition of fungi. (C) 2008 Elsevier Ltd. All rights reserved.
• 1 : 1 Adduct Ion Formation of Simple Carbohydrate Derivatives with Cations Using FAB Mass Spectrometry. Comparison of<i>O</i>-Acetyl,<i>N</i>-Butyl, and<i>O</i>-Methyl Modifications
  作者：Masami Sawada、Motohiro Shizuma、Yoshio Takai、Hitoshi Yamada、Takanori Tanaka、Yasuo Okumura、Yukio Hidaka、Terukiyo Hanafusa、Shigetoshi Takahashi

  DOI：10.1246/bcsj.65.1275

  日期：1992.5

  The 1 : 1 adduct ion formation between a series of per-O-acetylated aldopyranoses (family 1) or N-butylated glycosylamines (family 2) and an organic/metallic cation (n-C8H17NH3+/K+ or Li+) has been examined using quantitative FAB mass Spectrometry. The per-O-acetyl modifications dramatically lead to negated selectivity of the carbohydrates toward the cation which has been clearly observed in per-O-methyl modifications. On the other hand, the mono-N-butyl modifications provide a similar selectivity pattern to mono-O-methyl ones. These results are understood on the basis of electronic and structural considerations.

  使用 FAB 质谱法定量检测了一系列过-O-乙酰化醛吡喃糖（1 族）或 N-丁酰化糖基胺（2 族）与有机/金属阳离子（n-C8H17NH3+/K+ 或 Li+）之间形成的 1 : 1 加合物离子。过-O-乙酰基修饰显著降低了碳水化合物对阳离子的选择性，这一点在过-O-甲基修饰中也得到了清晰的观察。另一方面，单-N-丁基修饰提供了与单-O-甲基修饰相似的选择性模式。根据电子和结构方面的考虑，我们可以理解这些结果。
• Synthesis of<i>N</i>-Alkyl-β-<scp>d</scp>-glucosylamines and Their Antimicrobial Activity against<i>Fusarium proliferatum</i>,<i>Salmonella</i><i>typhimurium</i>, and<i>Listeria innocua</i>
  作者：T. Muhizi、S. Grelier、V. Coma

  DOI：10.1021/jf9016114

  日期：2009.12.9

  In this study, different N-alkyl-beta-D-glucosylamines were evaluated for both antifungal and antibacterial activity against Fusarium proliferatum (INRA, MUCL 1807.7), Listeria innocua (ISTAB, Universite Bordeaux 1), and Salmonella typhimurium (Institut Pasteur 5858). The tested glucosylamines were beta-D-glucosylamine (GPA), N-ethyl-beta-D-glucosylamine (EtGPA), N-butyl-beta-D-glucosylamine (BuGPA), N-hexyl-beta-D-glucosylamine (HeGPA), N-octyl-beta-D-glucosylamine (OcGPA), N-dodecyl-beta-D-glucosylamine (DoGPA), N-(2-hydroxyethyl)-beta-D-glucosylamine (HEtGPA), N,N-di(2-hydroxyethyl)-beta-D-glucosylamine (DHEtGPA) and N,N-diethyl-beta-D-glucosylamine (DEtGPA). The effectiveness of N-alkyl length, N-substitution, and N-hydroxyalkyl groups on both antibacterial and antifungal activity were evaluated. Results indicated that these compounds exhibited different biological activities and their effectiveness was highly increased from short to long N-alkyl chains. DoGPA exhibited more potent biological activity against all target strains than other N-alkyl glucosylamines tested. Using a radial growth method, we demonstrated that this compound completely inhibited fungal growth at 0.5 x 10(-4) mol mL(-1), while OcGPA and HeGPA lead to 71% and 43% fungal inhibition, respectively. Using the coating method, we demonstrated that DoGPA completely inhibited bacterial growth at 0.025 x 10(-4) and 0.05 x 10(-4) mol mL(-1) for L. innocua and S. typhimurium, respectively, while at the same concentrations, OcGPA exhibited weaker antibacterial activity of 12% and 27%, respectively, for L. innocua and S. typhimurium. The hole plate method enabled us to estimate the minimum inhibitory concentration (MIC) of DoGPA found to be 0.02 x 10(-4) and 0.025 x 10(-4) mol mL(-1) for L. innocua and S. typhimurium, respectively. Glucosylamines with N-hydroxyalkyl and short N-alkyl chains varying from C-2 to C-4 exhibited weaker antimicrobial activity.