methyl 6-azido-2,3-di-O-benzyl-6-deoxy-4-O-methyl-α-D-glucopyranoside | 193287-44-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-azido-2,3-di-O-benzyl-6-deoxy-4-O-methyl-α-D-glucopyranoside
• CAS: 193287-44-4
• 化学式: C₂₂H₂₇N₃O₅
• 分子量: 413.473
• InChiKey: MFOYBVNVNXTAMM-BDHVOXNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  30.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  94.91
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 6-azido-2,3-di-O-benzyl-6-deoxy-4-O-methyl-α-D-glucopyranoside 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以99%的产率得到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
• 作为产物：
  描述：

  methyl 2,3-di-O-benzyl-6-chloro-6-deoxy-4-O-methyl-α-D-glucopyranoside 在 sodium azide 、 1,1,3,3-四甲基脲 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以96%的产率得到methyl 6-azido-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