O-(3,4,6-tri-O-n-butyryl-2-deoxy-2-trichloracetamido-α-D-glucopyranosyl)-trichloroacetimidate | 222425-38-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(3,4,6-tri-O-n-butyryl-2-deoxy-2-trichloracetamido-α-D-glucopyranosyl)-trichloroacetimidate
• CAS: 222425-38-9
• 化学式: C₂₂H₃₀Cl₆N₂O₉
• 分子量: 679.206
• InChiKey: RUJHWBQBSYYKAD-QXWDTAIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  39.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  150.31
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  benzyl 5-O-benzyl-3-O-phenoxycarbonyl-D-β-glucofuranosiduronamide 、 O-(3,4,6-tri-O-n-butyryl-2-deoxy-2-trichloracetamido-α-D-glucopyranosyl)-trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 、 3 Angstroems MS 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 4.0h， 以68%的产率得到benzyl 2-O-(3,4,6-tri-O-n-butyryl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-5-O-benzyl-3-O-phenoxycarbonyl-α-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：

  1,3,4,6-tetra-O-n-butyryl-2-deoxy-2-trichloracetamido-D-glucopyranose 在 乙酸肼 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.83h， 生成 O-(3,4,6-tri-O-n-butyryl-2-deoxy-2-trichloracetamido-α-D-glucopyranosyl)-trichloroacetimidate
  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