N-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)chloroacetamide | 850813-89-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)chloroacetamide
• 英文别名: 2,3,4-tri-O-acetyl-β-D-xylopyranosyl chloroacetamide；N-(2,3,4-tri-O-acetyl-beta-d-xylopyranosyl) chloroacetamide；[(3R,4S,5R,6R)-4,5-diacetyloxy-6-[(2-chloroacetyl)amino]oxan-3-yl] acetate
• CAS: 850813-89-7
• 化学式: C₁₃H₁₈ClNO₈
• 分子量: 351.741
• InChiKey: OXLSNPKLUUGXEU-GWNIPJSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)chloroacetamide 在 sodium azide 、 sodium methylate 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 24.25h， 生成 N-(β-D-xylopyranosyl)azidoacetamide
  参考文献：
  名称：

  Synthesis ofN‐(β‐Glycopyrano‐syl)azidoacetamides

  摘要：

  N-(beta-Glycopyranosyl)azidoacetamides, mimetics of the widely distributed GlcNAc-Asn linkage in glycoproteins, have been synthesized in good yields starting from beta-glycopyranosylamines in four steps involving selective N-chloroacetylation, peracetylation catalyzed by Na beta-zeolite, displacement of the Cl group by NaN3 in aqueous acetone, and Zemplen de-O-acetylation.

  DOI：

  10.1081/car-200049402
• 作为产物：
  描述：

  β-D-xylopyranosylamine 在 Na β-zeolite 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 N-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)chloroacetamide
  参考文献：
  名称：

  Synthesis ofN‐(β‐Glycopyrano‐syl)azidoacetamides

  摘要：

  N-(beta-Glycopyranosyl)azidoacetamides, mimetics of the widely distributed GlcNAc-Asn linkage in glycoproteins, have been synthesized in good yields starting from beta-glycopyranosylamines in four steps involving selective N-chloroacetylation, peracetylation catalyzed by Na beta-zeolite, displacement of the Cl group by NaN3 in aqueous acetone, and Zemplen de-O-acetylation.

  DOI：

  10.1081/car-200049402

文献信息

• Synthesis and characterization of thiourea- and urea-linked glycolipids as low-molecular-weight hydrogelators
  作者：Manoharan Mathiselvam、Duraikkannu Loganathan、Babu Varghese

  DOI：10.1039/c3ra42041h

  日期：——

  hydrogelating ability as compared to thiourea linked glycolipids. The influence of sugar head group and alkyl chain length on the glycolipid’s self-assembly has also been studied. The fibrillar structures of the supramolecular hydrogels have been characterized by scanning electron microscopy (SEM). The thermal properties of the hydrogels formed by urea linked glycolipids have been studied by differential scanning

  通过使糖基氨基乙酰胺与烷基异硫氰酸酯和异氰酸酯反应，已经合成了具有硫脲和脲连接基的新型糖脂作为低分子量胶凝剂。研究了连接基团对其自组装性能的影响。对获得的新糖脂在各种溶剂中的胶凝研究表明，它们是良好的水凝剂。与硫脲连接的糖脂相比，尿素连接的糖脂显示出更好的水凝胶化能力。还研究了糖首基和烷基链长对糖脂自组装的影响。超分子水凝胶的原纤维结构已经通过扫描电子显微镜（SEM）表征。由尿素连接的糖脂形成的水凝胶的热性质已通过差示扫描量热法（DSC）和VT-NMR进行了研究。已经通过小角度（SAXS）和单晶X射线衍射方法研究了分子堆积。
• SnCl4/Sn catalyzed chemoselective reduction of glycopyranosyl azides for the synthesis of diversely functionalized glycopyranosyl chloroacetamides
  作者：Laxminarayan Sahoo、Anadi Singhamahapatra、Katuri J.V. Paul、Duraikkannu Loganathan

  DOI：10.1016/j.tetlet.2013.07.110

  日期：2013.9

  A method for the chemoselective reduction of glycopyranosyl azides using SnCl4 and tin metal as the reducing agent followed by in situ chloroacetylation of the synthesized glycopyranosyl amine was developed. This reaction is applicable to diversely functionalized glycopyranosyl azides for the synthesis of glycopyranosyl chloroacetamides. (C) 2013 Elsevier Ltd. All rights reserved.