N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) phenylacetamide | 439595-86-5

• 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-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) phenylacetamide
• 英文别名: 2,3,4,6-tetra-O-acetyl-1-N-phenyl acetyl-β-D-glucopyranosylamine；N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)benzeneacetamide；2-(phenyl)-N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) acetamide；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2-phenylacetyl)amino]oxan-2-yl]methyl acetate
• CAS: 439595-86-5
• 化学式: C₂₂H₂₇NO₁₀
• 分子量: 465.457
• InChiKey: UYUWWQIRTDDBMZ-MIUGBVLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  144
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) phenylacetamide 在 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 以86 %的产率得到N-(β-D-glucopyranosyl) phenylacetamide
  参考文献：
  名称：

  N-糖基酰胺的合成：构象分析和作为大肠杆菌 β-半乳糖苷酶抑制剂的评估

  摘要：

  N-糖基酰胺的合成通常涉及使用糖基胺作为直接前体，由于水解和异构化过程导致立体控制的损失，导致产率低。在这项研究中，提出了使用糖基胺作为从糖基叠氮化物获得的中间体，连续合成N-糖基酰胺。合成了具有葡萄糖、半乳糖或木糖构型的衍生物。在立体控制下获得的己糖衍生物仅产生β端基异构体，而木糖衍生物则提供α和β端基异构体的混合物。构象分析表明，所有β端基异构体均采用4 C 1构象，而α端基异构体则以1 C 4构象为主要构象。脱-O-乙酰化后，含有半乳糖单元的衍生物被评估为大肠杆菌β-半乳糖苷酶抑制剂，结果发现是中等抑制剂。

  DOI：

  10.1039/d3ra07763b
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl azide 在 三苯基膦 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 39.0h， 生成 N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) phenylacetamide
  参考文献：
  名称：

  Stereoselective Synthesis of α- and β-Glycosylamide Derivatives from Glycopyranosyl Azides via Isoxazoline Intermediates

  摘要：

  Treatment of 2-acetoxy glycopyranosyl azides with Ph3P gave isoxazolines by ring closure of the phosphorimine. Coupling of in situ generated isoxazolines with acylating reagents gave mixtures of alpha- or beta-glycopyranosyl amides. The alpha/beta ratio depended upon the acylating reagent and metal salts employed. For example, coupling of isoxazoline 3 with Z-Asp-(SPy)-OBn in the presence of CuCl2 gave exclusively alpha-N-glucopyranosylasparagine derivative 8. This general procedure has been applied to mono-, di-, and trisaccharide systems.

  DOI：

  10.1021/ja028694u

文献信息

• Synthesis of Glycosyl Amides Using Selenocarboxylates as Traceless Reagents for Amide Bond Formation
  作者：Luana Silva、Ricardo F. Affeldt、Diogo S. Lüdtke

  DOI：10.1021/acs.joc.6b00832

  日期：2016.7.1

  were successfully prepared in good yields from a broad range of substrates, including furanosyl and pyranosyl derivatives. The methodology successfully relied on the in situ generation of lithium selenocarboxylates from Se/LiEt3BH and acyl chlorides or carboxylic acids and their reaction with sugar azides. A key aspect of the present protocol is that we start from elemental selenium; isolation and handling

  从包括呋喃糖基和吡喃糖基衍生物在内的多种底物成功成功地制备了碳水化合物衍生的酰胺。该方法学成功地依赖于从Se / LiEt 3 BH和酰基氯或羧酸中原位生成硒酸锂锂，以及它们与糖叠氮化物的反应。本协议的一个关键方面是我们从元素硒开始。避免了所有反应性和敏感的含硒中间体的分离和处理，因此提供了硒代羧酸盐无痕试剂的状态。
• Synthesis of N-(β-D-glucopyranosyl)- and N-(2-acetamido-2-deoxy-β-D-glucopyranosyl) amides as inhibitors of glycogen phosphorylase
  作者：Zoltán Györgydeák、Zsuzsa Hadady、Nóra Felföldi、Attila Krakomperger、Veronika Nagy、Marietta Tóth、Attila Brunyánszki、Tibor Docsa、Pál Gergely、László Somsák

  DOI：10.1016/j.bmc.2004.07.013

  日期：2004.9

  2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl- and 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl azides were transformed into the corresponding per-O-acetylated N-(beta-D-glycopyranosyl) amides via a PMe3 mediated Staudinger protocol (generation of N-(beta-D-glycopyranosyl)imino-trimethylphosphoranes followed by acylation with carboxylic acids, acid chlorides or anhydrides). The deprotected compounds obtained by Zemplen deacetylation were evaluated as inhibitors of rabbit muscle glycogen phosphorylase b. The best inhibitor of this series has been N-(beta-D-glucopyranosyl) 3-(2-naphthyl)-propenoic amide (K-i = 3.5 muM). (C) 2004 Elsevier Ltd. All rights reserved.