benzyl 5-O-benzyl-3-O-phenoxycarbonyl-D-β-glucofuranosiduronamide | 222425-28-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 5-O-benzyl-3-O-phenoxycarbonyl-D-β-glucofuranosiduronamide
• CAS: 222425-28-7
• 化学式: C₂₇H₂₇NO₈
• 分子量: 493.513
• InChiKey: KYJFQAIMWYHYCG-WFMHDFSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  36.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  126.54
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  benzyl 5-O-benzyl-3-O-phenoxycarbonyl-D-β-glucofuranosiduronamide 在 三氟化硼乙醚 、 氨 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 45.0h， 生成 benzyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-O-benzyl-3-O-carbamoyl-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
• 作为产物：
  描述：

  5-O-benzyl-3-O-phenoxycarbonyl-D-glucofuranosiduronamide 、 苯甲醇 在 Dowex 50 WX₂ (H⁺ form) 作用下， 反应 7.0h， 以26%的产率得到benzyl 5-O-benzyl-3-O-phenoxycarbonyl-D-α-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