benzyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-O-benzyl-3-O-phenoxycarbonyl-β-D-glucofuranosiduronamide | 222425-32-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-O-benzyl-3-O-phenoxycarbonyl-β-D-glucofuranosiduronamide
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5S)-5-[(1S)-2-amino-2-oxo-1-phenylmethoxyethyl]-4-phenoxycarbonyloxy-2-phenylmethoxyoxolan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 222425-32-3
• 化学式: C₄₁H₄₅NO₁₇
• 分子量: 823.805
• InChiKey: JKRDVWYJRAHDEQ-WEKJWJOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  59.0
• 可旋转键数：
  17.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  229.97
• 氢给体数：
  1.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  benzyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-O-benzyl-3-O-phenoxycarbonyl-β-D-glucofuranosiduronamide 在 palladium dihydroxide 氨 、 氢气 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 36.0h， 生成 1,4-di-O-acetyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-O-carbamoyl-α-D-glucopyranuronamide
  参考文献：
  名称：

  Acceptor site recognition of transglycosylase inhibitors a β-D-glucopyranosyl-(1→2)-α-D-glucopyranuronamide-derived moenomycin analogue

  摘要：

  The synthesis, the antibiotic and the transglycosylase inibiting properties of a disaccharide analogue of moenomycin A in which the NHAc group of unit E is replaced by a hydroxyl function are described. It can be concluded that this NHAc group is essential for eliciting transglycosylase inhibiting properties, in agreement with a recently established solution structure of moenomycin A. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01181-8
• 作为产物：
  描述：

  5-O-benzyl-3-O-phenoxycarbonyl-D-glucofuranosiduronamide 在 Dowex 50 WX₂ (H⁺ form) 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 34.0h， 生成 benzyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-O-benzyl-3-O-phenoxycarbonyl-β-D-glucofuranosiduronamide
  参考文献：
  名称：

  Acceptor site recognition of transglycosylase inhibitors a β-D-glucopyranosyl-(1→2)-α-D-glucopyranuronamide-derived moenomycin analogue

  摘要：

  The synthesis, the antibiotic and the transglycosylase inibiting properties of a disaccharide analogue of moenomycin A in which the NHAc group of unit E is replaced by a hydroxyl function are described. It can be concluded that this NHAc group is essential for eliciting transglycosylase inhibiting properties, in agreement with a recently established solution structure of moenomycin A. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01181-8