methyl 6-(benzothiazol-2-yl)sulfonyl-6-deoxy-α-D-mannopyranoside | 226256-04-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-(benzothiazol-2-yl)sulfonyl-6-deoxy-α-D-mannopyranoside
• 英文别名: (2S,3S,4S,5S,6S)-2-(1,3-benzothiazol-2-ylsulfonylmethyl)-6-methoxyoxane-3,4,5-triol
• CAS: 226256-04-8
• 化学式: C₁₄H₁₇NO₇S₂
• 分子量: 375.423
• InChiKey: REUFWYUWTXBHPF-WSLQDRLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  163
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 6-(benzothiazol-2-yl)sulfonyl-6-deoxy-α-D-mannopyranoside 、 碘甲烷 在 potassium tert-butylate 作用下， 生成 methyl 3,4-di-O-acetyl-2-O-(benzothiazol-2-yl)-6-deoxy-6-methylsulfonyl-α-D-mannopyranoside 、 methyl 2,3-di-O-acetyl-4-O-(benzothiazol-2-yl)-6-deoxy-6-methylsulfonyl-α-D-mannopyranoside
  参考文献：
  名称：

  A New Intramolecular Migration in Thiosugar Chemistry: S → O Transfer of a Benzothiazol-2-Yl Group in Saccharidic Sulfones

  摘要：

  Saccharidic benzothiazol-2yl sulfones - readily obtained through regioselective Mitsunobu thiofunctionalization followed by standard S-oxidation - can easily undergo benzothiazol-2-yl group S --> O transfer when submitted to the action of a hindered base under controlled conditions. An ipso-substitution process is the key-step of this novel intramolecular rearrangement of saccharidic sulfones.

  DOI：

  10.1080/07328309908543998
• 作为产物：
  描述：

  methyl 6-S-(benzothiazol-2-yl)-6-thio-α-D-mannopyranoside 在 magnesium monoperoxyphthalate hexahydrate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.0h， 以72%的产率得到methyl 6-(benzothiazol-2-yl)sulfonyl-6-deoxy-α-D-mannopyranoside
  参考文献：
  名称：

  A New Intramolecular Migration in Thiosugar Chemistry: S → O Transfer of a Benzothiazol-2-Yl Group in Saccharidic Sulfones

  摘要：

  Saccharidic benzothiazol-2yl sulfones - readily obtained through regioselective Mitsunobu thiofunctionalization followed by standard S-oxidation - can easily undergo benzothiazol-2-yl group S --> O transfer when submitted to the action of a hindered base under controlled conditions. An ipso-substitution process is the key-step of this novel intramolecular rearrangement of saccharidic sulfones.

  DOI：

  10.1080/07328309908543998