methyl 1-S-acetyl-4,6-di-O-mesyl-1-thio-β-L-sorbofuranoside | 1025096-50-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 1-S-acetyl-4,6-di-O-mesyl-1-thio-β-L-sorbofuranoside
• CAS: 1025096-50-7
• 化学式: C₁₁H₂₀O₁₀S₃
• 分子量: 408.472
• InChiKey: BDAGMJZSULVOCB-VLEAKVRGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.31
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  142.5
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  methyl 1-S-acetyl-4,6-di-O-mesyl-1-thio-β-L-sorbofuranoside 在 碳酸氢钠 作用下， 以 乙二醇甲醚 、 水 为溶剂， 反应 22.0h， 以70%的产率得到methyl 1,4-anhydro-6-O-mesyl-1-thio-β-L-psicofuranoside
  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：

  1-O-acetyl-2,3-O-isopropylidene-4,6-di-O-mesyl-α-L-sorbofuranose 在 盐酸 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 114.0h， 生成 methyl 1-S-acetyl-4,6-di-O-mesyl-1-thio-β-L-sorbofuranoside
  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