N-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)azidoacetamide | 850813-95-5

• 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)azidoacetamide
• 英文别名: N-(2,3,4-tri-O-acetyl-beta-xylopyranosyl) azidoacetamide；[(3R,4S,5R,6R)-4,5-diacetyloxy-6-[(2-azidoacetyl)amino]oxan-3-yl] acetate
• CAS: 850813-95-5
• 化学式: C₁₃H₁₈N₄O₈
• 分子量: 358.308
• InChiKey: ODPJXEOLIVYUQY-GWNIPJSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  132
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)azidoacetamide 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以100%的产率得到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：

  2,3,4-tri-O-acetyl-β-D-xylopyranosylamine 在 sodium azide 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 生成 N-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)azidoacetamide
  参考文献：
  名称：

  硫脲和脲连接的糖脂作为低分子量水凝胶剂的合成与表征†

  摘要：

  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。

  DOI：

  10.1039/c3ra42041h

文献信息

• Synthesis of guanidino sugar conjugates as GlcβArg analogs
  作者：Amrita Srivastava、Duraikkannu Loganathan

  DOI：10.1007/s10719-013-9480-z

  日期：2013.11

  The β-glucosyl linkage to the guanidine group of arginine (Arg) is found in amylogenin, a glycoprotein from sweet corn. Such a linkage is formed by a rare N-glycosylation of proteins. Synthesis of analogs of the unusual N-glycosidic linkage (GlcβArg) with an acetamido or triazole spacer between the glycosyl residue and the guanidine moiety was accomplished by the reaction of fully acetylated sugar

  β-葡萄糖基与精氨酸 (Arg) 的胍基连接存在于淀粉原蛋白中，淀粉原蛋白是一种来自甜玉米的糖蛋白。这种连接是由蛋白质的罕见N-糖基化形成的。通过含有游离氨基的完全乙酰化糖单元与双 Boc-硫脲的反应，合成了不寻常的N-糖苷键 (GlcβArg)类似物，在糖基残基和胍部分之间具有乙酰氨基或三唑间隔基。在本研究期间还实现了具有酰胺接头的N-葡糖基精氨酸的合成。该方法还扩展到阳离子糖脂的合成。
• Synthesis of novel glycolipids derived from glycopyranosyl azides and N-(β-glycopyranosyl)azidoacetamides
  作者：Katuri J.V. Paul、Duraikkannu Loganathan

  DOI：10.1016/j.tetlet.2008.08.073

  日期：2008.10

  A general and expedient method based on a click reaction has been developed for the synthesis of novel glycolipids. The Cu(I) catalyzed [3+2] cycloaddition of several fully acetylated beta- as well as alpha-D-glycopyranosyl azides, including the 1,6-diazide derived from D-glucose, with long chain alkyl propargyl ethers gave the respective 1,4-substituted 1,2,3-triazole derivatives in good yields. Treatment of fully acetylated N-(beta-glycopyranosyl)azidoacetamides under similar conditions with alkyl propargyl ethers afforded the 1,2,3-triazolylacetamido derivatives in fairly good yields. Zemplen de-O-acetylation of all the fully acetylated derivatives furnished the free glycolipids in quantitative yields. (c) 2008 Elsevier Ltd. All rights reserved.