N-acetyl-β-D-glucopyranosylamine | 6983-36-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-acetyl-β-D-glucopyranosylamine
• 英文别名: 1-N-Acetyl-beta-D-Glucosamine；β-1-N-acetamido-D-glucopyranose；1-acetamido-1-deoxy-β-D-glucose；N-β-D-glucopyranosylacetamide；β-N-Acetyl D-glucosamine；N-Acetyl-β-D-glycopyranosyl amine；N-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]acetamide
• CAS: 6983-36-4
• 化学式: C₈H₁₅NO₆
• 分子量: 221.21
• InChiKey: IBONACLSSOLHFU-JAJWTYFOSA-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

• 作为反应物：
  描述：

  N-acetyl-β-D-glucopyranosylamine 在 sodium periodate 作用下， 生成 (S)-2-[(R)-1-acetylamino-2-(4-nitro-phenylhydrazono)-ethoxy]-3-hydroxy-propionaldehyde-(4-nitro-phenylhydrazone)
  参考文献：
  名称：

  Kawashiro, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1955, vol. 75, p. 101,103

  摘要：

  DOI：
• 作为产物：
  描述：

  1-acetamido-2,3,4,6-tetraacetyl-1-deoxy-β-D-glucopyranose 在 甲醇 、 barium methoxide 作用下， 生成 N-acetyl-β-D-glucopyranosylamine
  参考文献：
  名称：

  Mutarotation, Hydrolysis, and Rearrangement Reactions of Glycosylamines¹

  摘要：

  DOI：

  10.1021/jo01103a019

文献信息

• Inhibitors of human glycogen phosphorylase
  申请人：Pfizer Products Inc.

  公开号：EP0978279A1

  公开（公告）日：2000-02-09

  The present invention is directed to a novel binding site for a glycogen phosphorylase inhibitor found within a glycogen phosphorylase enzyme. The novel binding site allows the design novel of glycogen phosphorylase inhibitors.

  本发明涉及一种在糖原磷酸化酶酶内发现的新型糖原磷酸化酶抑制剂结合位点。该新型结合位点使得能够设计新型的糖原磷酸化酶抑制剂。
• The Reaction of Thio Acids with Azides:  A New Mechanism and New Synthetic Applications
  作者：Ning Shangguan、Sreenivas Katukojvala、Rachel Greenberg、Lawrence J. Williams

  DOI：10.1021/ja0294919

  日期：2003.7.1

  A new amide synthesis strategy based on a fundamental mechanistic revision of the reaction of thio acids and organic azides is presented. The data demonstrate that amines are not formed as intermediates in this reaction. Alternative mechanisms proceeding through a thiatriazoline intermediate are suggested. The reaction has been applied to the preparation of simple and architecturally complex amides

  提出了一种基于硫代酸和有机叠氮化物反应的基本机理修正的新酰胺合成策略。数据表明在该反应中没有形成胺作为中间体。建议了通过噻三唑啉中间体进行的替代机制。该反应已用于制备使用常规方法难以获得的简单且结构复杂的酰胺。该反应具有化学选择性，对未受保护的底物有效，并与非质子和质子溶剂（包括水）相容。
• Direct Preparation of N-Glycosidic Bond-Linked Nonionic Carbohydrate-Based Surfactant (NICBS) via Ritter Reaction
  作者：Zerong Daniel Wang、Samia O. Sheikh、Shannon Cox、Yulu Zhang、Keegan Massey

  DOI：10.1002/ejoc.200700079

  日期：2007.5

  The Ritter reaction has been successfully extended to the direct preparation of N-glycosidic bond-linked nonionic carbohydrate-based surfactants from carbohydrates and nitriles in the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) and silver perchlorate (AgClO4) on a high-speed mechanical shaker. The new surfactant molecules have the features of low toxicity, environmental compatibility

  Ritter 反应已成功扩展到在三氟甲磺酸三甲基甲硅烷基酯 (TMSOTf) 和高氯酸银 (AgClO4) 存在下，在高速机械振荡器上从碳水化合物和腈直接制备 N-糖苷键连接的非离子碳水化合物基表面活性剂。新型表面活性剂分子具有低毒、环境相容性和生物降解性等特点。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Model studies pertaining to the hydrazinolysis of glycopeptides and glycoproteins: hydrazinolysis of the 1-N-acetyl and 1-N-(l-β-aspartyl) derivatives of 2-acetamido-2-deoxy-β-d-glucopyranosylamine
  作者：May S. Saeed、J.Michael Williams

  DOI：10.1016/s0008-6215(00)85432-4

  日期：1980.9

  Abstract The products of hydrazinolysis of the 1- N -acetyl and 1- N -( l -β-aspartyl) derivatives of 2-acetamido-2-deoxy-β- d -glucopyranosylamine could not be converted quantitatively into 2-amino-2-deoxy- d -glucose under mild conditions. Proton and 13 C-n.m.r. measurements indicated that the hydrazone of 2-amino-2-deoxy- d -glucose was a major product of the hydrazinolysis of 2-acetamido-1- N -acetyl-2-deoxy-β-

  摘要2-乙酰氨基-2-脱氧-β-d-吡喃葡萄糖胺的1-N-乙酰基和1-N-（l-β-天冬氨酰）衍生物的肼解产物不能定量地转化为2-氨基-2 -脱氧-d-葡萄糖在温和的条件下。质子和13 Cn.mr测量表明2-氨基-2-脱氧-d-葡萄糖的zone是2-乙酰氨基-1-N-乙酰基-2-脱氧-β-d-吡喃葡萄糖胺的肼解作用的主要产物。对照实验表明，乙酰肼在肼解条件下缓慢转化为4-氨基-3,5-二甲基-1,2,4-三唑，2-氨基-2-脱氧-d-葡萄糖与乙酰肼反应缓慢。在稀乙酸中。讨论了这些结果与糖肽和糖蛋白的肼解作用有关。
• Chemoselective coupling of sugar oximes and α-ketoacids to glycosyl amides and N-glycopeptides
  作者：Claudia Pöhner、Vera Ullmann、Ramona Hilpert、Eric Samain、Carlo Unverzagt

  DOI：10.1016/j.tetlet.2014.02.056

  日期：2014.4

  The reaction of unprotected sugar hydroxylamines and oximes with α-ketoacids leads to the chemoselective formation of glycosyl amides following the decarboxylative condensation pathway of Bode’s ketoacid hydroxylamine (KAHA) ligation. Sugar oximes with gluco configuration stereoselectively form β-linked products. This method can be used for the convergent synthesis of N-acylated sugars and oligosaccharides

  未保护的糖羟胺和肟与α-酮酸的反应会导致Bode酮酸羟胺（KAHA）的脱羧缩合路径发生化学选择性的糖基酰胺形成。具有葡萄糖构型的糖肟立体选择性地形成β-连接的产物。该方法可用于收敛合成在酰基部分带有小标记，间隔基或肽的N-酰化糖和寡糖。