4-amino-1,2-O-isopropylidene-α-D-glucopyranose | 945743-63-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-amino-1,2-O-isopropylidene-α-D-glucopyranose
• CAS: 945743-63-5
• 化学式: C₉H₁₇NO₅
• 分子量: 219.238
• InChiKey: RHZGRHGMHIRJEJ-JAJWTYFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.46
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  94.17
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-amino-1,2-O-isopropylidene-α-D-glucopyranose 在 三乙胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Model for Antibiotic Optimization via Neoglycosylation:  Synthesis of Liponeoglycopeptides Active against VRE

  摘要：

  The neoglycosylation of a methoxyamine-appended vancomycin aglycon with all possible N'-decanoylglucopyranose and N'-biphenoylglucopyranose regioisomers led to the production of a focused set of liponeoglycopeptide variants in good yields and with excellent stereoselectivity. High-throughput antibacterial assays employing a unique set of vancomycin-resistant Enterococci faecalis and Enterococci faecium clinical isolates revealed that the nature and regiochemistry of glycosyl lipidation modulated vancomycin-resistent Enterococci potency. In contrast to prior work with lipoglycopeptides, this study reveals the glucose C3' or C4' as the optimal position for neoglycopeptide lipidation. This purely chemical method for the diversification of the glycolipid portion of lipoglycopeptide antibiotics is simple to perform on a large scale, requires minimal synthetic effort in sugar donor preparation, and provides access to highly active antibiotics that are not easily prepared by other state-of-the-art methods.

  DOI：

  10.1021/ja068602r
• 作为产物：
  描述：

  D-吡喃葡萄糖 在 palladium dihydroxide 吡啶 、 sodium azide 、 氢气 、 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.75h， 生成 4-amino-1,2-O-isopropylidene-α-D-glucopyranose
  参考文献：
  名称：

  Model for Antibiotic Optimization via Neoglycosylation:  Synthesis of Liponeoglycopeptides Active against VRE

  摘要：

  The neoglycosylation of a methoxyamine-appended vancomycin aglycon with all possible N'-decanoylglucopyranose and N'-biphenoylglucopyranose regioisomers led to the production of a focused set of liponeoglycopeptide variants in good yields and with excellent stereoselectivity. High-throughput antibacterial assays employing a unique set of vancomycin-resistant Enterococci faecalis and Enterococci faecium clinical isolates revealed that the nature and regiochemistry of glycosyl lipidation modulated vancomycin-resistent Enterococci potency. In contrast to prior work with lipoglycopeptides, this study reveals the glucose C3' or C4' as the optimal position for neoglycopeptide lipidation. This purely chemical method for the diversification of the glycolipid portion of lipoglycopeptide antibiotics is simple to perform on a large scale, requires minimal synthetic effort in sugar donor preparation, and provides access to highly active antibiotics that are not easily prepared by other state-of-the-art methods.

  DOI：

  10.1021/ja068602r