1-S-(benzothiazol-2-yl)-2,3-O-isopropylidene-1-thio-L-sorbofuranose | 226256-02-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-S-(benzothiazol-2-yl)-2,3-O-isopropylidene-1-thio-L-sorbofuranose
• 英文别名: (3aR,5S,6R,6aS)-3a-(1,3-benzothiazol-2-ylsulfanylmethyl)-5-(hydroxymethyl)-2,2-dimethyl-6,6a-dihydro-5H-furo[2,3-d][1,3]dioxol-6-ol
• CAS: 226256-02-6
• 化学式: C₁₆H₁₉NO₅S₂
• 分子量: 369.463
• InChiKey: JFYFKFSPJOIWPI-GXCBOPRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  135
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-S-(benzothiazol-2-yl)-2,3-O-isopropylidene-1-thio-L-sorbofuranose 在 potassium tert-butylate 、 magnesium monoperoxyphthalate hexahydrate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 6-O-(benzothiazol-2-yl)-1-deoxy-2,3-O-isopropylidene-1-methylsulfonyl-L-sorbofuranose
  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：

  1-S-benzothiazol-2-yl-2,3:4,6-di-O-isopropylidene-1-thio-L-sorbofuranose 在 溶剂黄146 作用下， 反应 1.0h， 以90%的产率得到1-S-(benzothiazol-2-yl)-2,3-O-isopropylidene-1-thio-L-sorbofuranose
  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

文献信息

• A New Intramolecular Migration in Thiosugar Chemistry: S → O Transfer of a Benzothiazol-2-Yl Group in Saccharidic Sulfones
  作者：David Gueyrard、Christelle Lorin、Patrick Rollin、Jitka Moravcova

  DOI：10.1080/07328309908543998

  日期：1999.1.1

  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.