4-azido-1,2,3,6-tetra-O-benzoyl-D-glucopyranose | 945743-59-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-azido-1,2,3,6-tetra-O-benzoyl-D-glucopyranose
• 英文别名: 4-azido-4-deoxy-1,2,3,6-tetra-O-benzoyl-D-glucopyranose；1-O-Acetyl-4-azido-2,3,6-tri-O-benzoyl-4-deoxy-D-glucopyranose；[(2S,3R,4S,5R)-3-azido-4,5,6-tribenzoyloxyoxan-2-yl]methyl benzoate
• CAS: 945743-59-9
• 化学式: C₃₄H₂₇N₃O₉
• 分子量: 621.603
• InChiKey: LYACDXDOAMGFAL-RIKJQNKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.56
• 重原子数：
  46.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  163.19
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  4-azido-1,2,3,6-tetra-O-benzoyl-D-glucopyranose 在 palladium dihydroxide 氢气 、 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.75h， 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
• 作为产物：
  描述：

  D-吡喃葡萄糖 在 吡啶 、 sodium azide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 4-azido-1,2,3,6-tetra-O-benzoyl-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

文献信息

• Synthesis of azido-deoxy and amino-deoxy glycosides and glycosyl fluorides for screening of glycosidase libraries and assembly of substituted glycosides
  作者：Hong-Ming Chen、Stephen G. Withers

  DOI：10.1016/j.carres.2018.07.007

  日期：2018.9

  useful tools in the probing of biological systems as well as in the assembly of libraries of derivatives using click chemistry or simple amine coupling approaches. A collection of methylumbelliferyl glycosides of various azido- and amino-deoxy sugar derivatives of glucose, galactose and xylose was synthesised via azide displacement of the corresponding triflate derivatives and subsequent modification.

  叠氮化物和胺取代的糖在探测生物系统以及使用点击化学或简单的胺偶联方法组装衍生物库中可能是有用的工具。通过叠氮化物置换相应的三氟甲磺酸衍生物并随后进行修饰，合成了葡萄糖，半乳糖和木糖的各种叠氮基和氨基脱氧糖衍生物的甲基伞形糖苷苷。这些化合物将在高通量筛选中用作底物，以鉴定可加工此类修饰糖的糖苷酶。还合成了每种修饰糖的α-糖基氟衍生物，以用作衍生自筛选中鉴定的酶的糖合酶底物。