sodium dodecyl β-D-glucopyranoside 6-sulfate | 126872-46-6

• 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 β-D-glucopyranoside 6-sulfate
• 英文别名: n-dodecyl β-D-glucopyranoside 6-hydrogen sulfate monosodium salt；sodium;[(2R,3S,4S,5R,6R)-6-dodecoxy-3,4,5-trihydroxyoxan-2-yl]methyl sulfate
• CAS: 126872-46-6
• 化学式: C₁₈H₃₅O₉S*Na
• 分子量: 450.526
• InChiKey: UIDIMWOEGOUWFJ-MFOMZMTJSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.79
• 重原子数：
  29
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  154
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

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

  十二烷基吡喃葡萄糖苷 在 吡啶 、 三氧化硫吡啶 、 碳酸氢钠 作用下， 以 水 为溶剂， 反应 7.0h， 以67%的产率得到sodium dodecyl β-D-glucopyranoside 6-sulfate
  参考文献：
  名称：

  新型6-硫酸盐糖基阴离子表面活性剂的合成及界面性质

  摘要：

  合成了三族在单糖的主要位置上带有硫酸盐官能团的阴离子糖基表面活性剂，并比较了它们的理化性质。第一家庭对应于市售的八- 6-硫酸衍生物和十二烷基β- d -葡糖- 和吡喃半乳糖苷。第二个和第三个家族在硫酸化单糖（半乳糖、葡萄糖或木糖）和疏水性烷基链之间包含一个酰胺接头。研究了 12 种合成的阴离子糖脂（包括 9 种新型硫酸化化合物）在空气/液体界面的表面活性和自组装性能。这些糖基表面活性剂的表面特性与商业阴离子表面活性剂（SDS 和 SLES）相似，具有良好的降低表面张力的能力。获得的结果证实了人们对这些新的生物基分子在各种配方中潜在替代阴离子表面活性剂的兴趣。

  DOI：

  10.1016/j.tetlet.2021.153113

文献信息

• Glucopyranoside-Based Surfactants as Pseudostationary Phases for Chiral Separations in Capillary Electrophoresis
  作者：David C. Tickle、George N. Okafo、Patrick. Camilleri、Rose F. D. Jones、Anthony J. Kirby

  DOI：10.1021/ac00095a002

  日期：1994.12.1

  Dodecyl beta-D-glucopyranoside monophosphate and monosulfate anionic surfactants have been synthesized and used successfully in micellar electrokinetic capillary chromatography for the separation of enantiomers. These surfactants have low critical micelle concentrations of about 0.5 and 1.0 mM, respectively. The methodology developed is applicable to chiral molecules differing widely in chemical structure, hydrophobicity, and acidity. The use of these surfactants extends the usefulness of CE as a tool for chiral separations, complementary to other techniques such as thin-layer chromatography and high-performance liquid chromatography.