2-acetamido-2-deoxy-3-O-allyl-4,6-O-(phenylmethylene)-β-D-glucopyranosylazide | 1452848-73-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 2-acetamido-2-deoxy-3-O-allyl-4,6-O-(phenylmethylene)-β-D-glucopyranosylazide
• 英文别名: N-[(2R,4aR,6R,7R,8R,8aS)-6-azido-2-phenyl-8-prop-2-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide
• CAS: 1452848-73-5
• 化学式: C₁₈H₂₂N₄O₅
• 分子量: 374.396
• InChiKey: TUASEOJDNWKJMN-TYENPDHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  80.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-acetamido-2-deoxy-3-O-allyl-4,6-O-(phenylmethylene)-β-D-glucopyranosylazide 、 氯乙酰氯 在 tin 、 四氯化锡 、 sodium sulfate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以95%的产率得到N-{2-acetamido-2-deoxy-3-O-allyl-4,6-O-(phenylmethylene)-β-D-glucopyranosyl}chloroacetamide
  参考文献：
  名称：

  SnCl4/Sn catalyzed chemoselective reduction of glycopyranosyl azides for the synthesis of diversely functionalized glycopyranosyl chloroacetamides

  摘要：

  A method for the chemoselective reduction of glycopyranosyl azides using SnCl4 and tin metal as the reducing agent followed by in situ chloroacetylation of the synthesized glycopyranosyl amine was developed. This reaction is applicable to diversely functionalized glycopyranosyl azides for the synthesis of glycopyranosyl chloroacetamides. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.110
• 作为产物：
  描述：

  2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-Β-D-吡喃葡萄糖酰基叠氮化物 在 sodium methylate 、 sodium hydride 、 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 120.0h， 生成 2-acetamido-2-deoxy-3-O-allyl-4,6-O-(phenylmethylene)-β-D-glucopyranosylazide
  参考文献：
  名称：

  SnCl4/Sn catalyzed chemoselective reduction of glycopyranosyl azides for the synthesis of diversely functionalized glycopyranosyl chloroacetamides

  摘要：

  A method for the chemoselective reduction of glycopyranosyl azides using SnCl4 and tin metal as the reducing agent followed by in situ chloroacetylation of the synthesized glycopyranosyl amine was developed. This reaction is applicable to diversely functionalized glycopyranosyl azides for the synthesis of glycopyranosyl chloroacetamides. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.110