methyl 6-O-octyl α-D-glucopyranoside | 142025-36-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-O-octyl α-D-glucopyranoside
• 英文别名: (2S,3R,4S,5S,6R)-2-methoxy-6-(octoxymethyl)oxane-3,4,5-triol
• CAS: 142025-36-3
• 化学式: C₁₅H₃₀O₆
• 分子量: 306.4
• InChiKey: YDFXYULZFYYCHL-QMIVOQANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 6-O-octyl α-D-glucopyranoside 在 甲醇 、 三氟甲磺酸酐 、 sodium methylate 、 乙酸酐 作用下， 生成 C6-O-octyl-D-glucose
  参考文献：
  名称：

  Amphiphilic and mesogenic carbohydrates - II. sysnthesis and Characterisation of mono-o-(n-alkyl)-d-glucose derivates

  摘要：

  The synthesis of various amphiphilic o-(n-alkyl)-D-glucopyranoses, having the long alkyl chain (C8H17 - C16H33) in 2-, 3-, 4- or 6-position are described. The investigations of the thermal behaviour of 6-o-(13a-e), 4-o-(14a-e), 3-o-(15a-e) and 2-o-(n-alkyl)-D-glucopyranoses (16a-e) and the corresponding methyl-alpha-D-glucosides 4a-e, 8a-e and 12a-e, respectively, are summarized in this paper.

  DOI：

  10.1016/s0040-4020(01)92248-3
• 作为产物：
  描述：

  甲基-6-O-三苯基甲基-alpha-D-吡喃葡萄糖苷 在 甲酸 、 palladium on activated charcoal 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 paraffin oil 为溶剂， 反应 28.25h， 生成 methyl 6-O-octyl α-D-glucopyranoside
  参考文献：
  名称：

  甲基葡苯二糖苷的羟烷基醚的疏水性和亲水性平衡及其对中间相行为的影响

  摘要：

  制备了四个系列的单取代甲基α- D-吡喃葡萄糖苷羟烷基醚，并根据其疏水-亲水平衡对其分子结构进行了研究，研究了它们的热致和溶致自组织特性。获得的结果使我们对驱动凝聚软物质相形成的力有了新的认识。

  DOI：

  10.1002/chem.201202933

文献信息

• Synthesis, surfactant properties and antimicrobial activities of methyl glycopyranoside ethers
  作者：Dorine Belmessieri、Charlotte Gozlan、Marie-Christine Duclos、Valérie Molinier、Jean-Marie Aubry、Oana Dumitrescu、Gérard Lina、Andreas Redl、Nicolas Duguet、Marc Lemaire

  DOI：10.1016/j.ejmech.2017.01.038

  日期：2017.3

  A series of amphiphilic methyl glucopyranoside ethers incorporating various alkyl chain lengths has been synthesized from commercially available methyl glucopyranosides following an acetalisation/hydrogenolysis sequence. The amphiphilic properties of ethers and acetal intermediates were evaluated. Both families exhibit excellent surfactant properties with a maximum efficiency obtained for compounds

  按照缩醛化/氢解顺序，已经从市售的甲基吡喃葡萄糖苷合成了一系列结合了各种烷基链长的两亲性甲基吡喃葡萄糖苷醚。评估了醚和乙缩醛中间体的两亲性。这两个家族均表现出优异的表面活性剂性能，对于带有线性十二烷基链的化合物（CMC = 0.012 mM，γsat。  = 30 mN m -1）具有最大的效率。抗菌活性研究表明，它对革兰氏阳性细菌（如单核细胞增生性李斯特菌，粪肠球菌，粪肠球菌和金黄色葡萄球菌）具有有效活性（0.03
• Catalytic reductive cleavage of methyl α-<scp>d</scp>-glucoside acetals to ethers using hydrogen as a clean reductant
  作者：Charlotte Gozlan、Romain Lafon、Nicolas Duguet、Andreas Redl、Marc Lemaire

  DOI：10.1039/c4ra09350j

  日期：——

  The palladium-catalysed reductive cleavage of methyl glucoside acetals has been studied using hydrogen as a clean reducing agent. The reaction proceeds at 120 °C in cyclopentyl methyl ether (CPME) without acid co-catalyst. Under these conditions, the corresponding methyl glucoside monoethers were obtained with poor to good isolated yields (37–81%) and high selectivities (86–99%).

  使用氢作为清洁的还原剂，已经研究了钯催化的甲基葡萄糖苷乙缩醛的还原裂解。该反应在120°C的环戊基甲基醚（CPME）中进行，没有酸助催化剂。在这些条件下，获得了相应的甲基葡糖苷单醚，分离产率差至好（37-81％），选择性高（86-99％）。
• TMDS as a Dual-Purpose Reductant in the Regioselective Ring Cleavage of Hexopyranosyl Acetals to Ethers
  作者：Yin-Jie Zhang、Wissam Dayoub、Guo-Rong Chen、Marc Lemaire

  DOI：10.1002/ejoc.201101682

  日期：2012.4

  1,1,3,3-Tetramethyldisiloxane (TMDS) has been developed as an excellent dual-purpose reductant for the highly regioselective ring cleavage of various hexopyranosyl 4,6-O-acetals with Cu(OTf)2 or AlCl3 to afford the corresponding primary and secondary ethers. Its application to the concise synthesis of carbohydrate-based surfactants is highlighted.

  1,1,3,3-四甲基二硅氧烷 (TMDS) 已被开发为一种优异的双用途还原剂，用于各种吡喃己糖基 4,6-O-缩醛与 Cu(OTf)2 或 AlCl3 的高区域选择性环裂解，以提供相应的初级和次级醚。强调了其在碳水化合物基表面活性剂的简明合成中的应用。
• An easy route to methyl 6-O-alkyl glycosides
  作者：Corinne Bayle、Andrée Gadelle

  DOI：10.1016/0040-4039(94)85213-8

  日期：1994.4

  Methyl 6-O-alkyl-glucopyranosides were obtained in excellent yield from methyl 6-deoxy-6-iodoglucopyranoside and the appropriate alcohol in the presence of chlorine.

  6- ø -烷基吡喃葡萄糖苷是在良好的收率由甲基-6-脱氧-6- iodoglucopyranoside和在氯的存在下适当的醇而获得。
• Hydrophobic and Hydrophilic Balance and Its Effect on Mesophase Behaviour in Hydroxyalkyl Ethers of Methyl Glucopyranoside
  作者：Madan K. Singh、Rui Xu、Sylvie Moebs、Anil Kumar、Yves Queneau、Stephen J. Cowling、John W. Goodby

  DOI：10.1002/chem.201202933

  日期：2013.4.15

  Four series of monosubstituted methyl α‐D‐glucopyranoside hydroxyalkyl ethers were prepared and their thermotropic and lyotropic self‐organising properties were investigated in terms of the hydrophobic–hydrophilic balance with respect to their molecular structures. The results obtained lead us to a new understanding of the forces that drive the formation of condensed soft‐matter phases.

  制备了四个系列的单取代甲基α- D-吡喃葡萄糖苷羟烷基醚，并根据其疏水-亲水平衡对其分子结构进行了研究，研究了它们的热致和溶致自组织特性。获得的结果使我们对驱动凝聚软物质相形成的力有了新的认识。