2-methyl-7-(2-acetamido-2-deoxy-β-D-glucopyranosyloxy)isoflavone | 388582-46-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 2-methyl-7-(2-acetamido-2-deoxy-β-D-glucopyranosyloxy)isoflavone
• 英文别名: (2-methyl-3-phenylchromonyl-7)-2-acetamido-2-deoxy-β-D-glucopyranoside；2-methyl-4-oxo-3-phenyl-4H-chromen-7-yl 2-(acetylamino)-2-deoxy-beta-D-glucopyranoside；N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(2-methyl-4-oxo-3-phenylchromen-7-yl)oxyoxan-3-yl]acetamide
• CAS: 388582-46-5
• 化学式: C₂₄H₂₅NO₈
• 分子量: 455.464
• InChiKey: NTSAVLDATFYUQZ-YFBZVTLSSA-N

物化性质

• 沸点：
  770.1±60.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-methyl-7-(2-acetamido-2-deoxy-β-D-glucopyranosyloxy)isoflavone 在 N-羟基丁二酰亚胺 、 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 7.08h， 生成
  参考文献：
  名称：

  摘要：

  The synthesis of beta-(2-methyl-3-phenylchromonyl-7)- and beta-[2-methyl-3-(3,4-trimethylenedioxy) phenylchromonyl-7]glycosides of the methyl ester of N-acetylmuramoyl-L-alanyl-D-isoglutamine, new derivatives of a muramoyldipeptide with chromone aglycones, is described. The starting arylglycosides of N-acetylglucosamine are prepared by glycosylation of 7-hydroxychromone derivatives with the peracetate of alpha -glucosamine chloride catalyzed by a crown ether. The synthesized beta -aryl-4,6-O-isopropylidene-N-acetylmuramic acids are condensed with the dipeptide and deprotected to give the desired glycopeptides.

  DOI：

  10.1023/a:1017694224906
• 作为产物：
  描述：

  2-乙酰氨基-3,4,6-三-O-乙酰-2-脱氧-α-D-吡喃葡萄糖酰基氯 在 15-冠醚-5 、 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 12.0h， 生成 2-methyl-7-(2-acetamido-2-deoxy-β-D-glucopyranosyloxy)isoflavone
  参考文献：
  名称：

  摘要：

  beta-0-Glycosides of N-acetylglucosamine with substituted 7-hydroxychromones and 7-hydroxycoumarins as the aglycones are synthesized The phenyl hydroxyls are O-glycosylated in a solid-liquid system with crown-ether catalysts. The structures of the chromone and coumarin N-acetylglucosaminides and their per-0-acetates are proved by PMR spectroscopy.

  DOI：

  10.1023/a:1019635914082

文献信息

• ——
  作者：A. E. Zemlyakov、V. O. Kur'yanov、T. A. Chupakhina、V. Ya. Chirva、V. V. Ishchenko、M. M. Garazd、V. P. Khilya

  DOI：10.1023/a:1019635914082

  日期：——

  beta-0-Glycosides of N-acetylglucosamine with substituted 7-hydroxychromones and 7-hydroxycoumarins as the aglycones are synthesized The phenyl hydroxyls are O-glycosylated in a solid-liquid system with crown-ether catalysts. The structures of the chromone and coumarin N-acetylglucosaminides and their per-0-acetates are proved by PMR spectroscopy.
• ——
  作者：V. O. Kur'yanov、T. A. Chupakhina、A. E. Zemlyakov、V. Ya. Chirva、V.V. Ishchenko、V. P. Khilya

  DOI：10.1023/a:1017694224906

  日期：——

  The synthesis of beta-(2-methyl-3-phenylchromonyl-7)- and beta-[2-methyl-3-(3,4-trimethylenedioxy) phenylchromonyl-7]glycosides of the methyl ester of N-acetylmuramoyl-L-alanyl-D-isoglutamine, new derivatives of a muramoyldipeptide with chromone aglycones, is described. The starting arylglycosides of N-acetylglucosamine are prepared by glycosylation of 7-hydroxychromone derivatives with the peracetate of alpha -glucosamine chloride catalyzed by a crown ether. The synthesized beta -aryl-4,6-O-isopropylidene-N-acetylmuramic acids are condensed with the dipeptide and deprotected to give the desired glycopeptides.