methyl 6-amino-2,3-di-O-benzyl-6-deoxy-4-O-methyl-α-D-glucopyranoside | 193287-46-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-amino-2,3-di-O-benzyl-6-deoxy-4-O-methyl-α-D-glucopyranoside
• CAS: 193287-46-6
• 化学式: C₂₂H₂₉NO₅
• 分子量: 387.476
• InChiKey: OSOKJHVNHKRUJL-BDHVOXNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  28.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  72.17
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 6-amino-2,3-di-O-benzyl-6-deoxy-4-O-methyl-α-D-glucopyranoside 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 1.0h， 生成 N-(methyl 6-deoxy-4-O-methyl-α-D-glucopyranoside-6-ylaminocarbonyl)-L-aspartic acid
  参考文献：
  名称：

  Synthesis of novel amino acid glycoside conjugates

  摘要：

  A new class of non-anomeric amino acid glycoconjugates can be prepared starting from either omega-amino- or omega-halodeoxyglucosides. Treatment of an ether-protected methyl 7-amino-6,7-dideoxy-alpha-D-glucoheptopyranoside with methyl aspartate isocyanate gave an urea-linked conjugate of methyl glucoheptopyranoside and aspartic acid. Nucleophilic displacement of the ether-protected methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside with potassium succinimide followed by imide ring opening and amidation of the succinic acid monoamide with dimethyl iminodiacetate led to a conjugate of methyl 6-amino-6-deoxy-alpha-D-glucopyranoside and iminodiacetate bridged by succinate. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00091-8
• 作为产物：
  描述：

  methyl 2,3-di-O-benzyl-6-chloro-6-deoxy-α-D-glucopyranoside 在 palladium on activated charcoal sodium hydroxide 、 sodium azide 、 氢气 、 三乙胺 、 1,1,3,3-四甲基脲 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 methyl 6-amino-2,3-di-O-benzyl-6-deoxy-4-O-methyl-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of novel amino acid glycoside conjugates

  摘要：

  A new class of non-anomeric amino acid glycoconjugates can be prepared starting from either omega-amino- or omega-halodeoxyglucosides. Treatment of an ether-protected methyl 7-amino-6,7-dideoxy-alpha-D-glucoheptopyranoside with methyl aspartate isocyanate gave an urea-linked conjugate of methyl glucoheptopyranoside and aspartic acid. Nucleophilic displacement of the ether-protected methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside with potassium succinimide followed by imide ring opening and amidation of the succinic acid monoamide with dimethyl iminodiacetate led to a conjugate of methyl 6-amino-6-deoxy-alpha-D-glucopyranoside and iminodiacetate bridged by succinate. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00091-8