tetradecyl-(O⁴-β-D-glucopyranosyl-β-D-glucopyranoside) | 122119-57-7

• 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: tetradecyl-(O⁴-β-D-glucopyranosyl-β-D-glucopyranoside)
• 英文别名: Tetradecyl-(O⁴-β-D-glucopyranosyl-β-D-glucopyranosid)；(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-tetradecoxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 122119-57-7
• 化学式: C₂₆H₅₀O₁₁
• 分子量: 538.676
• InChiKey: UKPROSIGWJBJGA-RMQXEJAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  37
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  179
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  乙酰溴代纤维二糖 在 calcium sulfate 、 碘 、 正丁胺 、 silver carbonate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 66.0h， 生成 tetradecyl-(O⁴-β-D-glucopyranosyl-β-D-glucopyranoside)
  参考文献：
  名称：

  Thermotropic Liquid Crystals Based on Oligosaccharides.n-Alkyl 1-O-β-D-Cellobiosides

  摘要：

  合成了碳数范围在7到18之间的n-烷基-1-O-β-D-纤维二糖苷,并与已知的单糖同系物n-烷基-1-O-β-D-吡喃葡萄糖苷进行了热性能比较研究。研究发现,纤维二糖苷在比葡萄糖苷更高的温度下表现出热致介晶相。根据烷基链长和热历史的不同,纤维二糖苷呈现出均向性、短暂的杆状、多边形和扇形等不同织构。与单糖同系物类似,由于样品取向困难,无法对介晶相进行完整分类,但未取向纤维二糖苷的X射线衍射图谱表明其介晶相属于层状A相(或较小可能为层状C相)。层厚度随烷基链长的变化比单糖同系物弱得多(约为后者的一半)。文中还提出了纤维二糖苷在介晶相中可能的分子排列方式。

  DOI：

  10.1246/bcsj.67.346

文献信息

• Micelle-mediated multicomponent cross-coupling in water: general construction of 3-chalcogenylindoles
  作者：Xi He、Weili Song、Xuemin Liu、Jiamin Huang、Ruilong Feng、Shaodong Zhou、Jianquan Hong、Xin Ge

  DOI：10.1039/d2gc03694k

  日期：——

  A general and sustainable multicomponent cross-coupling for the construction of 3-chalcogenylindoles from indoles with aryl iodides and elemental sulfur under the aqueous micellar condition was developed. Elemental sulfur is employed as an eco-friendly and easy-handling sulfur source of thiyl radicals. The synergic effect between Cu catalysts and micelles formed by the sugar-based surfactant GluM can

  开发了一种通用且可持续的多组分交叉偶联，用于在水性胶束条件下从吲哚与芳基碘化物和元素硫构建 3-硫属吲哚。元素硫被用作一种环保且易于处理的硫自由基硫源。Cu 催化剂和糖基表面活性剂 GluM 形成的胶束之间的协同作用可以稳定硫自由基，进一步通过单电子转移在容易获得的吲哚上引发 C-S 偶联。值得注意的是，水性胶束系统不仅可以回收再利用，收率高，而且还可以扩展到元素硒的转化。
• Hori, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1958, vol. 78, p. 999,1001
  作者：Hori

  DOI：——

  日期：——
• Thermotropic Liquid Crystals Based on Oligosaccharides.<i>n</i>-Alkyl 1-<i>O</i>-<i>β</i>-D-Cellobiosides
  作者：Yung-Dae Ma、Akihiko Takada、Makoto Sugiura、Takeshi Fukuda、Takeaki Miyamoto、Junji Watanabe

  DOI：10.1246/bcsj.67.346

  日期：1994.2

  n-Alkyl 1-O-β-d-cellobiosides with an alkyl length ranging from 7 to 18 in carbon number m were synthesized, and their thermal properties were studied in comparison with those of the already-known monosaccharide homologues, n-alkyl 1-O-β-d-glucopyranosides. The cellobiosides were found to exhibit a thermotropic mesophase at higher temperatures than the glucopyranosides. Depending on m and thermal history, the cellobiosides showed various textures such as homeotropic, transient bâtonnets, polygonal, and fan-shaped textures. Like in the case of the monosaccharide homologues, the difficulty of aligning the samples prohibited a full classification of the mesophase, but the X-ray diffractograms of the unaligned cellobiosides indicated that their mesophase belongs to smectic A(or less possibly, smectic C). The m dependence of the lamella thickness was much weaker than (about half) that of the monosaccharide homologues. Possible molecular arrangements of the cellobiosides in the mesophase were presented.

  合成了碳数范围在7到18之间的n-烷基-1-O-β-D-纤维二糖苷,并与已知的单糖同系物n-烷基-1-O-β-D-吡喃葡萄糖苷进行了热性能比较研究。研究发现,纤维二糖苷在比葡萄糖苷更高的温度下表现出热致介晶相。根据烷基链长和热历史的不同,纤维二糖苷呈现出均向性、短暂的杆状、多边形和扇形等不同织构。与单糖同系物类似,由于样品取向困难,无法对介晶相进行完整分类,但未取向纤维二糖苷的X射线衍射图谱表明其介晶相属于层状A相(或较小可能为层状C相)。层厚度随烷基链长的变化比单糖同系物弱得多(约为后者的一半)。文中还提出了纤维二糖苷在介晶相中可能的分子排列方式。