Methyl 2-benzamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside | 4288-73-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: Methyl 2-benzamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside
• 英文别名: N-[(4aR,6S,7R,8R,8aS)-8-hydroxy-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]benzamide
• CAS: 4288-73-7
• 化学式: C₂₁H₂₃NO₆
• 分子量: 385.417
• InChiKey: HLPAFJDBUQIFPH-CBUBUMAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 2-benzamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 在 四丁基氟化铵 、 sodium hydride 、 溶剂黄146 作用下， 以 吡啶 、 六甲基磷酰三胺 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 25.5h， 生成 methyl 2-benzamido-4-O-benzoyl-3-O-benzyl-2,6-dideoxy-6-fluoro-α-D-galactopyranoside
  参考文献：
  名称：

  Hough, Leslie; Penglis, Anna A. E.; Richardson, Anthony C., Canadian Journal of Chemistry, 1981, vol. 59, p. 396 - 405

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲醛二甲缩醛 、 Methyl 2-benzamido-2-deoxy-α-D-glucopyranoside 在 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 生成 Methyl 2-benzamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of methyl 3-N-benzoyl-4-O-benzoyl-β-l-daunosaminide

  摘要：

  DOI：

  10.1016/0008-6215(84)85317-3

文献信息

• Synthesis of New Pseudodisaccharide Aminoglycoside Antibiotics from Carbohydrates.
  作者：ISTVÁN F. PELYVÁS、MÁRIA MÁDI-PUSKÁS、ZOLTÁN G. TÓTH、ZSOLT VARGA、MIKLÓS HORNYÁK、GYULA BATTA、FERENC SZTARICSKAI

  DOI：10.7164/antibiotics.48.683

  日期：——

  Novel pseudodisaccharide-type aminocyclitol antibiotic models, built up from D-arabinose, D-ribose, D-glucosamine, L-ristosamine and L-acosamine have been synthesized by the glycosylation of. suitably protected (azido)deoxyinosose aglycones derived by the Ferrier carbocyclic ring transformation of carbohydrate precursors. An alternative approach to related pseudodisaccharides, based on the Ferrier carbocyclization of reducing disaccharides, has also been elaborated. This latter method extends the scope of the Ferrier reaction, by demonstrating that acid-labile 2-deoxydisaccharides can also be readily transformed into the corresponding pseudodisaccharides under the slightly acidic conditions of this ring-transformation.

  通过糖基化反应，合成了由D-阿拉伯糖、D-核糖、D-葡糖胺、L-里斯托糖胺和L-阿科糖胺构成的新型pseudo二糖型氨基环醇抗生素模型。这些合成过程利用了从碳水化合物前体通过费里尔碳环变换得到的适当保护的(叠氮)去氧肌醇苷元。基于费里尔碳环化的还原二糖的另一种相关pseudo二糖合成方法也得到了详细阐述。这种方法通过展示在稍微酸性条件下，不稳定的2-脱氧二糖也能容易地转化为相应的pseudo二糖，从而扩展了费里尔反应的应用范围。
• Synthesis of <scp>d</scp>-Fructofuranosides Using Thioglycosides as Glycosyl Donors
  作者：Christian Krog-Jensen、Stefan Oscarson

  DOI：10.1021/jo951641t

  日期：1996.1.1

  Benzylated and benzoylated ethyl thioglycosides of D-fructofuranose have been synthesized and tested as glycosyl donors in couplings to various primary and secondary carbohydrate accepters. Treatment of 2-O-acetyl-1,3,4,6-tetra-O-benzoyl-D-fructofuranose with ethyl mercaptan in a BF3 .-etherate-promoted reaction gave the benzoylated ethyl 2-thio-alpha,beta-D-fructofuranosides, which after deacylation and benzylation afforded the benzylated derivatives. These thiofructofuranosides, using dimethyl(methylthio)sulfonium triflate (DMTST) or N-iodosuccinimide as promoter, were found to be excellent donors, which gave disaccharide coupling products in quantitative or almost quantitative yields with all tested accepters, yields rarely found in oligosaccharide synthesis. The benzoylated donors gave only alpha-linked fructofuranosides, due to participation of the 3-O-benzoyl group, whereas the benzylated donors gave alpha/beta-mixtures.
• Hough, Leslie; Penglis, Anna A. E.; Richardson, Anthony C., Canadian Journal of Chemistry, 1981, vol. 59, p. 396 - 405
  作者：Hough, Leslie、Penglis, Anna A. E.、Richardson, Anthony C.

  DOI：——

  日期：——
• Synthesis of methyl 3-N-benzoyl-4-O-benzoyl-β-l-daunosaminide
  作者：Mukund K. Gurjar、Vijay J. Patil、Jhillu S. Yadav、A.V. Rama Rao

  DOI：10.1016/0008-6215(84)85317-3

  日期：1984.7