methyl 4-O-pentyl α-D-glucopyranoside | 131940-76-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-pentyl α-D-glucopyranoside
• 英文别名: (2S,3R,4R,5S,6R)-6-(hydroxymethyl)-2-methoxy-5-pentoxyoxane-3,4-diol
• CAS: 131940-76-6
• 化学式: C₁₂H₂₄O₆
• 分子量: 264.319
• InChiKey: DCRALCSLPVEFBQ-OOCWMUITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  18
• 可旋转键数：
  7
• 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

• 作为产物：
  描述：

  methyl 4,6-O-pentylidene-α-D-glucoside 在 1,1,3,3-四甲基二硅氧烷 、 Cu(OTf)2 作用下， 以 二氯甲烷 为溶剂， 以42%的产率得到methyl 4-O-pentyl α-D-glucopyranoside
  参考文献：
  名称：

  TMDS 在吡喃己糖基缩醛到醚的区域选择性环裂解中作为双用途还原剂

  摘要：

  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。

  DOI：

  10.1002/ejoc.201101682

文献信息

• SYNTHESIS OF MONOETHERS OF SUGAR COMPRISING A LONG ALKYL CHAIN AND USES THEREOF AS A SURFACTANT
  申请人：TEREOS STARCH & SWEETENERS BELGIUM

  公开号：US20180265533A1

  公开（公告）日：2018-09-20

  A process for obtaining a mixture of C4-C8 and C9-C18 alkyl monoether of saccharide, comprising: a) a first step of acetalization or trans-acetalization of a saccharide or of a mixture of saccharides with a C4-C8 aliphatic aldehyde or the acetal thereof, b) a second consecutive or simultaneous step of acetalization or trans-acetalization of the product obtained in a) of the saccharide or mixture of saccharides with a C9-C18 aliphatic aldehyde or the acetal thereof, c) a step of catalytic hydrogenolysis of the saccharide acetals obtained, and d) a step of recovery of a mixture of C4-C8 and C9-C18 alkyl saccharide monoethers. The invention further relates to a mixture of C4-C8 and C9-C18 alkyl saccharide monoethers and the use thereof as a surfactant.

  一种获取C4-C8和C9-C18糖苷烷基单醚混合物的方法，包括：a)对糖苷或糖苷混合物与C4-C8脂肪族醛或其缩醛进行缩醛化或转缩醛化的第一步骤，b)对步骤a)中得到的糖苷或糖苷混合物与C9-C18脂肪族醛或其缩醛进行连续或同时的缩醛化或转缩醛化的第二步骤，c)对所得糖苷缩醛进行催化氢解的步骤，以及d)回收C4-C8和C9-C18糖苷烷基单醚混合物的步骤。该发明还涉及一种C4-C8和C9-C18糖苷烷基单醚混合物及其作为表面活性剂的用途。
• ANTIBACTERIAL COMPOSITION CONTAINING AN ISOMER MIXTURE OF MONOSACCHARIDE ALKYL MONOACETALS OR MONOETHERS
  申请人：TEREOS STARCH & SWEETENERS BELGIUM

  公开号：US20170347653A1

  公开（公告）日：2017-12-07

  A bactericidal or bacteriostatic composition comprising an isomer mixture of monosaccharide alkyl monoethers or monoacetals, its use in the treatment or prevention of Gram-positive bacterial infections, its use as a hygiene or dermatological product for external use and a method for disinfecting surfaces.

  一种杀菌或抑菌组合物，包括单糖烷基单醚或单缩醛的异构体混合物，其用于治疗或预防革兰氏阳性细菌感染，其用作外用卫生或皮肤学产品，以及一种消毒表面的方法。
• 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。