benzyl 4-azido-2-O-benzoyl-4-deoxy-α-D-rhamnopyranoside | 1284280-87-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 4-azido-2-O-benzoyl-4-deoxy-α-D-rhamnopyranoside
• 英文别名: [(2S,3S,4S,5S,6R)-5-azido-4-hydroxy-6-methyl-2-phenylmethoxyoxan-3-yl] benzoate
• CAS: 1284280-87-0
• 化学式: C₂₀H₂₁N₃O₅
• 分子量: 383.404
• InChiKey: DTOJPXZRQGFSRG-KVSMCJPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  79.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  benzyl 3,4-anhydro-6-deoxy-α-D-talopyranoside 在 吡啶 、 叠氮基三甲基硅烷 、 三氟化硼乙醚 作用下， 反应 3.0h， 生成 benzyl 4-azido-2-O-benzoyl-4-deoxy-α-D-rhamnopyranoside
  参考文献：
  名称：

  An efficient synthesis of selectively functionalized d-rhamnose derivatives

  摘要：

  D-Rhamnose is an important component of bacterial lipopolysaccharides. This paper describes a short and highly efficient synthesis of D-rhamnose from D-mannose. The synthesis of selectively C-4 modified D-rhamnosides and 6-deoxy-D-talosides as potential building blocks for complex oligosaccharide synthesis is also discussed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.064

文献信息

• An efficient synthesis of selectively functionalized d-rhamnose derivatives
  作者：Matthew Zunk、Milton J. Kiefel

  DOI：10.1016/j.tetlet.2011.01.064

  日期：2011.3

  D-Rhamnose is an important component of bacterial lipopolysaccharides. This paper describes a short and highly efficient synthesis of D-rhamnose from D-mannose. The synthesis of selectively C-4 modified D-rhamnosides and 6-deoxy-D-talosides as potential building blocks for complex oligosaccharide synthesis is also discussed. (C) 2011 Elsevier Ltd. All rights reserved.