N-acetyl-α-D-glucopyranosylamide | 76094-79-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-acetyl-α-D-glucopyranosylamide
• 英文别名: N-acetyl-α-D-glucopyranosylamine；N-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]acetamide
• CAS: 76094-79-6
• 化学式: C₈H₁₅NO₆
• 分子量: 221.21
• InChiKey: IBONACLSSOLHFU-CBQIKETKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  119
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,3,4,6-四邻乙酰基-beta-d-吡喃葡萄糖氯化物 在 platinum(IV) oxide 吡啶 、 甲醇 、 sodium azide 、 氢气 、 三乙胺 作用下， 以 甲醇 、 六甲基磷酰三胺 为溶剂， 反应 24.5h， 生成 N-acetyl-α-D-glucopyranosylamide
  参考文献：
  名称：

  The nephritogenic glycopeptide from rat glomerular basement membrane: synthesis of α-D-glucopyranosylamine derivatives

  摘要：

  N-(L-β-天冬氨酸-α-D-葡萄糖吡喃糖胺)已经被制备出来，作为大鼠肾小球基底膜可能存在的对应衍生物的模型。方法是在二乙基氰磷酰胺的存在下，将α-乙基苄氧羰基-L-天冬酸与2,3,4,6-四-O-乙酰基-α-D-葡萄糖吡喃糖胺缩合。然后通过氢解、去乙酰化和去乙氧基化，去除保护基，得到2,3,4,6-四-O-乙酰基-N-(α-乙基苄氧羰基-L-β-天冬氨酸-α-D-葡萄糖吡喃糖胺)。分析和讨论了相应的糖胺衍生物的13C NMR光谱。

  DOI：

  10.1139/v80-415

文献信息

• Traceless Staudinger Ligation of Glycosyl Azides with Triaryl Phosphines:  Stereoselective Synthesis of Glycosyl Amides
  作者：Aldo Bianchi、Anna Bernardi

  DOI：10.1021/jo060409s

  日期：2006.6.1

  α-Glycosyl amides can be synthesized from the corresponding O-benzyl-α-glycosyl azides using a traceless Staudinger ligation with diphenylphosphanyl-phenyl esters 4. All the phosphines employed and their phenol precursors are stable to air at 4 °C for months. Fast intramolecular trapping of the reduction intermediates results in the direct formation of the amide link, which, in turn, prevents epimerisation

  α-糖基酰胺可通过无痕施陶丁格与二苯基膦酰基-苯基酯的连接由相应的O-苄基-α-糖基叠氮化物合成4。所用的所有膦及其苯酚前体在4°C的空气中均可保持稳定数月。还原中间体的快速分子内捕集导致酰胺键的直接形成，继而防止了差向异构化并允许在异头碳上保留构型。当反应在极性非质子溶剂中进行时，产率和α-选择性高。苄基醚保护基的去除是通过催化氢化来实现的。α-糖基酰胺代表了一类实际上未开发的不可水解的单糖衍生物，可以作为糖模拟物找到有用的应用。NMR光谱的构象研究证实，葡萄糖，半乳糖和fuco系列中的脱保护α-糖基酰胺保留了单糖的正常吡喃糖构象。膦的反应4用四ø -乙酰基葡糖基叠氮化物是nonstereoconservative，并在良好的产率，并与来自两个α和β叠氮化物开始完整的立体选择性获得β糖基酰胺。
• Stereoselective synthesis of glycosyl amides by traceless Staudinger ligation of unprotected glycosyl azides
  作者：Filippo Nisic、Anna Bernardi

  DOI：10.1016/j.carres.2008.04.023

  日期：2008.7

  The stereoconservative Staudinger ligation of unprotected alpha- and beta-glucosyl azides with diphenylphosphanyl-phenyl esters to afford alpha- and beta-glucosyl amides is described.

  描述了未保护的α-和β-葡糖基叠氮化物与二苯基膦基-苯基酯的立体保守Staudinger连接，得到α-和β-葡糖基酰胺。
• α-Glucopyranoimidazolines as intermediate analogue inhibitors of family 20 β-N-acetylglucosaminidases
  作者：Masahiro Kato、Tetsuya Uno、Jun Hiratake、Kanzo Sakata

  DOI：10.1016/j.bmc.2004.12.017

  日期：2005.3.1

  The alpha-glucopyranoimidazolines, 2-methyl-(1,2-dideoxy-alpha-D-glucopyrano)[2,1-d]-1-imidazolines 1 and 2, have been synthesized and evaluated as inhibitors of beta-N-acetylglucosaminidases (NAGs). Compounds I and 2, mimicking the oxazolinium ion intermediate in enzyme catalysis, served as potent and competitive inhibitors of family 20 NAGs with K-i as low as 0.1 muM, but showed no inhibitory activities toward family 3 NAGs. Due to structural and electrostatic resemblance to the oxazolinium ion intermediate, the alpha-glucopyranoimidazolines may lead to novel and selective inhibitors of mechanistically related glycosidases such as family 18 chitinases. (C) 2004 Elsevier Ltd. All rights reserved.
• The nephritogenic glycopeptide from rat glomerular basement membrane: synthesis of α-<scp>D</scp>-glucopyranosylamine derivatives
  作者：Tadahiro Takeda、Yoshihiro Sugiura、Yukio Ogihara、Seiichi Shibata

  DOI：10.1139/v80-415

  日期：1980.12.1

  N-(L-β-aspartyl)-α-D-glucopyranosylamine has been prepared, as a model of a corresponding derivative possibly present in glomerular basement membrane of rats, by the condensation of α-ethyl benzyloxycarbonyl-L-aspartate with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosylamine in the presence of diethylphosphorocyanidate. This was followed by hydrogenolysis, de-O-acetylation, and deethoxylation of the resulting 2,3,4,6-tetra-O-acetyl-N-(α-ethyl benzyloxycarbonyl-L-β-aspartyl)-α-D-glucopyranosylamine to remove the protecting groups. The ¹³C nmr spectra of the corresponding glycosylamine derivatives are analyzed and discussed.

  N-(L-β-天冬氨酸-α-D-葡萄糖吡喃糖胺)已经被制备出来，作为大鼠肾小球基底膜可能存在的对应衍生物的模型。方法是在二乙基氰磷酰胺的存在下，将α-乙基苄氧羰基-L-天冬酸与2,3,4,6-四-O-乙酰基-α-D-葡萄糖吡喃糖胺缩合。然后通过氢解、去乙酰化和去乙氧基化，去除保护基，得到2,3,4,6-四-O-乙酰基-N-(α-乙基苄氧羰基-L-β-天冬氨酸-α-D-葡萄糖吡喃糖胺)。分析和讨论了相应的糖胺衍生物的13C NMR光谱。