benzyl 3,4-anhydro-2-O-benzoyl-6-deoxy-α-D-talopyranoside | 1284280-85-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl 3,4-anhydro-2-O-benzoyl-6-deoxy-α-D-talopyranoside
• 英文别名: [(1S,2R,4S,5S,6S)-2-methyl-4-phenylmethoxy-3,7-dioxabicyclo[4.1.0]heptan-5-yl] benzoate
• CAS: 1284280-85-8
• 化学式: C₂₀H₂₀O₅
• 分子量: 340.376
• InChiKey: BKMVPCLONCTKBM-NBZNJJEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  57.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl 3,4-anhydro-2-O-benzoyl-6-deoxy-α-D-talopyranoside 在 叠氮基三甲基硅烷 、 三氟化硼乙醚 作用下， 反应 1.0h， 以59%的产率得到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
• 作为产物：
  描述：

  1-O-benzyl-2,3-O-isopropylidene-α-D-rhamnopyranoside 在 吡啶 、 sodium azide 作用下， 以 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.17h， 生成 benzyl 3,4-anhydro-2-O-benzoyl-6-deoxy-α-D-talopyranoside
  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.