(2S,3R,4R,5S,6R)-3-azido-5-(benzyloxy)-6-(hydroxymethyl)-2-(p-tolylthio)tetrahydro-2H-pyran-4-yl acetate | 1386972-44-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4R,5S,6R)-3-azido-5-(benzyloxy)-6-(hydroxymethyl)-2-(p-tolylthio)tetrahydro-2H-pyran-4-yl acetate
• CAS: 1386972-44-6
• 化学式: C₂₂H₂₅N₃O₅S
• 分子量: 443.524
• InChiKey: PYJFPMNAXMUCJB-LMYCIYFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  113.75
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5S,6R)-3-azido-5-(benzyloxy)-6-(hydroxymethyl)-2-(p-tolylthio)tetrahydro-2H-pyran-4-yl acetate 在 咪唑 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成
  参考文献：
  名称：

  Solid-Phase Synthesis of 2-Aminoethyl Glucosamine Sulfoforms

  摘要：

  Mono- and disaccharides of sulfonated glucosamines (GlcN sulfoforms) conjugated to 2-aminoethyl linkers were generated by solid-phase synthesis. Orthogonally protected intermediates were tethered onto tritylated polystyrene resin beads, subjected to a modular sequence of deprotection and sulfonation steps, then cleaved from solid support without degradation of N- or O-sulfate esters using solvolytic conditions, and finally purified by reverse-phase HPLC to afford the title compounds.

  DOI：

  10.1080/07328303.2012.658274
• 作为产物：
  描述：

  p-tolyl 2-deoxy-2-azido-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 在 吡啶 、 2,6-二甲基吡啶 、 三氟甲磺酸二丁硼 、 diborane(6) 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 生成 (2S,3R,4R,5S,6R)-3-azido-5-(benzyloxy)-6-(hydroxymethyl)-2-(p-tolylthio)tetrahydro-2H-pyran-4-yl acetate
  参考文献：
  名称：

  Solid-Phase Synthesis of 2-Aminoethyl Glucosamine Sulfoforms

  摘要：

  Mono- and disaccharides of sulfonated glucosamines (GlcN sulfoforms) conjugated to 2-aminoethyl linkers were generated by solid-phase synthesis. Orthogonally protected intermediates were tethered onto tritylated polystyrene resin beads, subjected to a modular sequence of deprotection and sulfonation steps, then cleaved from solid support without degradation of N- or O-sulfate esters using solvolytic conditions, and finally purified by reverse-phase HPLC to afford the title compounds.

  DOI：

  10.1080/07328303.2012.658274