methyl 5-S-acetyl-1,3,4-tri-O-mesyl-5-thio-β-D-fructopyranoside | 1025096-32-5

• 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: methyl 5-S-acetyl-1,3,4-tri-O-mesyl-5-thio-β-D-fructopyranoside
• CAS: 1025096-32-5
• 化学式: C₁₂H₂₂O₁₂S₄
• 分子量: 486.563
• InChiKey: FZRNQARXUXUTAD-WISYIIOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.33
• 重原子数：
  28.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  165.64
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  methyl 5-S-acetyl-1,3,4-tri-O-mesyl-5-thio-β-D-fructopyranoside 在 sodium sulfide 作用下， 以 二甲基亚砜 为溶剂， 反应 20.0h， 以5%的产率得到methyl 1,5-anhydro-3,4-di-O-mesyl-1-thio-β-D-fructopyranoside
  参考文献：
  名称：

  Preparation of Anhydro-Thiohexopyranosides and -Thiohexofuranosides with D-fructo-, L-sorbo-, L-psico- and L-tagato-Configuration Starting from L-Sorbose

  摘要：

  Methyl alpha- L-sorbopyranoside is transformed into the bicyclic thiosugar methyl 1,5-anhydro-3,4-di-O-mesyl-1-thio-beta-D-fructopyranoside in two steps, whereas the corresponding 3-O-benzoate is obtained from methyl 1,3-O-benzylidene-alpha-L-sorbopyranoside in three steps. 2,3-O-Isopropylidenesorbofuranosides, on the other hand, can be transformed into 6-S-thioacetates by use of the thio-Mitsunobu reaction. These are suitable precursors for the preparation of 1,6-anhydro-1-thiosorbofuranosides. Also, methyl 1-S-acetyl-1-thio-L-sorbofuranosides with mesylate leaving groups are available by the thio-Mitsunobu reaction. They yield 1,4-anhydro-1-thio-beta-L-tagatofuranosides, 1,3-anhydro-alpha-L-psicofuranosides and 1,6-anhydro-1-thio-alpha-L-sorbofuranosides depending on the configuration of the starting compound. Attempts to prepare azido-thio-sugars by displacement of mesylate groups with alkali metal azides failed.

  DOI：

  10.1080/10426500701340915
• 作为产物：
  描述：

  methyl α-L-sorbopyranoside 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 生成 methyl 5-S-acetyl-1,3,4-tri-O-mesyl-5-thio-β-D-fructopyranoside
  参考文献：
  名称：

  Preparation of Anhydro-Thiohexopyranosides and -Thiohexofuranosides with D-fructo-, L-sorbo-, L-psico- and L-tagato-Configuration Starting from L-Sorbose

  摘要：

  Methyl alpha- L-sorbopyranoside is transformed into the bicyclic thiosugar methyl 1,5-anhydro-3,4-di-O-mesyl-1-thio-beta-D-fructopyranoside in two steps, whereas the corresponding 3-O-benzoate is obtained from methyl 1,3-O-benzylidene-alpha-L-sorbopyranoside in three steps. 2,3-O-Isopropylidenesorbofuranosides, on the other hand, can be transformed into 6-S-thioacetates by use of the thio-Mitsunobu reaction. These are suitable precursors for the preparation of 1,6-anhydro-1-thiosorbofuranosides. Also, methyl 1-S-acetyl-1-thio-L-sorbofuranosides with mesylate leaving groups are available by the thio-Mitsunobu reaction. They yield 1,4-anhydro-1-thio-beta-L-tagatofuranosides, 1,3-anhydro-alpha-L-psicofuranosides and 1,6-anhydro-1-thio-alpha-L-sorbofuranosides depending on the configuration of the starting compound. Attempts to prepare azido-thio-sugars by displacement of mesylate groups with alkali metal azides failed.

  DOI：

  10.1080/10426500701340915