sodium dodecyl α-D-glucopyranoside 6-sulfate | 149405-95-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: sodium dodecyl α-D-glucopyranoside 6-sulfate
• CAS: 149405-95-8
• 化学式: C₁₈H₃₅O₉S*Na
• 分子量: 450.526
• InChiKey: UIDIMWOEGOUWFJ-JOWXCZTESA-M

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 sodium dodecyl α-D-glucopyranoside 6-sulfate 在 吡啶 作用下， 反应 24.0h， 生成 sodium dodecyl 2,3,4-tri-O-acetyl-α-D-glucopyranoside 6-sulfate
  参考文献：
  名称：

  Synthesis and properties of sulfated alkyl glycosides

  摘要：

  Alkyl glycosides were sulfated with sulfur trioxide-pyridine. Dodecyl alpha- and beta-D-glucopyranoside gave the corresponding 6-sulfates in 75 and 51% yields, respectively. Separation from polysulfated compounds was carried out by reversed-phase HPLC. Tetradecyl beta-maltopyranoside (16) gave a 88 : 12 mixture of 6'- and 6-sulfates. The sulfated compounds were characterized by H-1-, C-13-, and 2-dimensional NMR spectroscopy. Surfactant and thermotropic liquid-crystalline properties of the sugar derivatives were examined. All of the glycosides show smectic phases (S(A)), and the clearing points rise by introduction of sulfate groups. Even glycosides having no unprotected hydroxy groups may show S(A)-phases when bearing sulfate groups. The mesomorphic properties cannot be explained by formation of distinct aggregates, but rather must be interpreted by an effective intramolecular contrast.

  DOI：

  10.1016/0008-6215(92)84036-r
• 作为产物：
  描述：

  十二烷基 alpha-D-吡喃葡萄糖苷 在 吡啶 、 sodium hydroxide 、 三氧化硫 作用下， 生成 sodium dodecyl α-D-glucopyranoside 6-sulfate
  参考文献：
  名称：

  Synthesis and properties of sulfated alkyl glycosides

  摘要：

  Alkyl glycosides were sulfated with sulfur trioxide-pyridine. Dodecyl alpha- and beta-D-glucopyranoside gave the corresponding 6-sulfates in 75 and 51% yields, respectively. Separation from polysulfated compounds was carried out by reversed-phase HPLC. Tetradecyl beta-maltopyranoside (16) gave a 88 : 12 mixture of 6'- and 6-sulfates. The sulfated compounds were characterized by H-1-, C-13-, and 2-dimensional NMR spectroscopy. Surfactant and thermotropic liquid-crystalline properties of the sugar derivatives were examined. All of the glycosides show smectic phases (S(A)), and the clearing points rise by introduction of sulfate groups. Even glycosides having no unprotected hydroxy groups may show S(A)-phases when bearing sulfate groups. The mesomorphic properties cannot be explained by formation of distinct aggregates, but rather must be interpreted by an effective intramolecular contrast.

  DOI：

  10.1016/0008-6215(92)84036-r