n-dodecyl β-D-cellobioside | 74513-19-2

• 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: n-dodecyl β-D-cellobioside
• 英文别名: n-dodecyl β-D-glucopyranosyl-(1->4)-β-D-glucopyranoside；dodecyl-β-cellobioside；n-dodecyl β-D-maltoside；n-dodecyl β-maltoside；dodecyl-(O⁴-β-D-glucopyranosyl-β-D-glucopyranoside)；Dodecyl-(O⁴-β-D-glucopyranosyl-β-D-glucopyranosid)；dodecyl-β-D-maltoside；dodecyl-D-maltoside；Dodecyl beta-d-cellobioside；(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-6-dodecoxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 74513-19-2
• 化学式: C₂₄H₄₆O₁₁
• 分子量: 510.623
• InChiKey: NLEBIOOXCVAHBD-ALYNCGSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  35
• 可旋转键数：
  16
• 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 n-dodecyl β-D-cellobioside
  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
• 作为试剂：
  描述：

  1-deoxy-1-fluoro-α-D-glucopyranuronic acid ammonium salt 、 1-萘甲醇 在 Escherichia coli glucuronylsynthase mutant E₅₀₄G 、 n-dodecyl β-D-cellobioside 作用下， 反应 96.0h， 以48%的产率得到1'-naphthalenemethyl β-D-glucopyranosiduronic acid
  参考文献：
  名称：

  Escherichia coli Glucuronylsynthase:  An Engineered Enzyme for the Synthesis of β-Glucuronides

  摘要：

  The glycosynthase derived from E coli beta-glucuronidase catalyzes the glucuronylation of a range of primary, secondary, and aryl alcohols with moderate to excellent yields. The procedure provides an efficient, stereoselective, and scalable single-step synthesis of 6-glucuronides under mild conditions.

  DOI：

  10.1021/ol8002767

文献信息

• Simple preparations of alkyl and cycloalkyl α-glycosides of maltose, cellobiose, and lactose
  作者：Shinkiti Koto、Motoko Hirooka、Takako Tashiro、Motokazu Sakashita、Masaharu Hatachi、Takayuki Kono、Miho Shimizu、Nahoko Yoshida、Sayaka Kurasawa、Natsuko Sakuma、Sunao Sawazaki、Akihiro Takeuchi、Naomi Shoya、Emi Nakamura

  DOI：10.1016/j.carres.2004.07.016

  日期：2004.10

  allyl, 4-pentenyl, and benzyl α-glycosides of maltose, cellobiose, and lactose were prepared (17–77% yield; α/β = 70/30–96/4) via a direct reaction of the free disaccharides with a binary AcBr–AcOH mixture, followed by glycosidation with alcohol using FeCl3 in MeNO2 or CH2Cl2, Zemplen deacetylation, and resolution of the anomeric mixture of glycosides by chromatography. Using MeCN as solvent for the

  摘要麦芽糖，纤维二糖和乳糖的烷基，环烷基，烯丙基，4-戊烯基和苄基α-糖苷的制备是（17-77％的收率；α/β= 70 / 30-96 / 4）。游离的二糖与二元AcBr-AcOH混合物混合，然后使用FeNO3在MeNO2或CH2Cl2中与酒精进行糖基化，Zemplen脱乙酰化，并通过色谱分离糖苷的异头混合物。使用MeCN作为糖苷化步骤的溶剂，还制备了相应的β-生物苷（16-61％产率；α/β= 25 / 75-5 / 95）。
• Alkyl melibioside and alkyl cellobioside surfactants: effect of sugar headgroup and alkyl chain length on performance
  作者：Laurel L. Kegel、Lajos Z. Szabó、Robin Polt、Jeanne E. Pemberton

  DOI：10.1039/c6gc00436a

  日期：——

  The potential of glycolipid surfactants, composed of a sugar headgroup and lipid tail, as highly biodegradable and less toxic alternatives to commonly used surfactants motivates the systematic study of structure–function relationships of various glycolipid surfactants.

  糖脂表面活性剂具有潜在的应用价值，由糖基和脂肪尾部组成，具有高度可生物降解性和低毒性，可作为常用表面活性剂的替代品。这促使对不同糖脂表面活性剂的结构-功能关系进行系统研究。
• 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。