2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4-O-acetyl-3-O-carbamoyl-1-O-<<(R)-2-methoxycarbonyl-2-(3,8,8,11,14,18-hexamethylnonadecyloxy)-ethoxy>-(2,2,2-trichloro-1,1-dimethylethyloxy)-phosphoryl>-α-D-glucopyranuronamide | 222639-02-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4-O-acetyl-3-O-carbamoyl-1-O-<<(R)-2-methoxycarbonyl-2-(3,8,8,11,14,18-hexamethylnonadecyloxy)-ethoxy>-(2,2,2-trichloro-1,1-dimethylethyloxy)-phosphoryl>-α-D-glucopyranuronamide
• 英文别名: methyl (2R)-3-[[(2R,3R,4S,5S,6S)-5-acetyloxy-6-carbamoyl-4-carbamoyloxy-3-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-(1,1,1-trichloro-2-methylpropan-2-yl)oxyphosphoryl]oxy-2-(3,8,8,11,14,18-hexamethylnonadecoxy)propanoate
• CAS: 222639-02-3
• 化学式: C₅₆H₉₄Cl₃N₂O₂₃P
• 分子量: 1300.69
• InChiKey: HLVQVODYMGMJAG-LOYAELPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  85.0
• 可旋转键数：
  37.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  334.89
• 氢给体数：
  2.0
• 氢受体数：
  23.0

反应信息

• 作为反应物：
  描述：

  2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4-O-acetyl-3-O-carbamoyl-1-O-<<(R)-2-methoxycarbonyl-2-(3,8,8,11,14,18-hexamethylnonadecyloxy)-ethoxy>-(2,2,2-trichloro-1,1-dimethylethyloxy)-phosphoryl>-α-D-glucopyranuronamide 在 lithium hydroxide 、 铜 、 乙酰丙酮 、 锌 作用下， 以 吡啶 、 甲醇 、 水 为溶剂， 反应 2.0h， 生成 2-O-(β-D-glucopyranosyl)-3-O-carbamoyl-1-O-<<(R)-2-carboxy-2-(3,8,8,11,14,18-hexamethylnonadecyloxy)-ethoxy>-hydroxyphosphoryl>-α-D-glucopyranuronic acid
  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：

  2,2,2-trichloro-1,1-dimethylethyl dichlorophosphite 、 Methyl (R)-2-(3,8,8,11,11,14,18-hexamethylnonadecyloxy-3-hydroxypropionate) 、 2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4-O-acetyl-3-O-carbamoyl-α-D-glucopyranuronamide 生成 2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4-O-acetyl-3-O-carbamoyl-1-O-<<(R)-2-methoxycarbonyl-2-(3,8,8,11,14,18-hexamethylnonadecyloxy)-ethoxy>-(2,2,2-trichloro-1,1-dimethylethyloxy)-phosphoryl>-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