Methyl (octyl β-D-glucopyranosid)uronate | 148312-83-8

• 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: Methyl (octyl β-D-glucopyranosid)uronate
• 英文别名: octyl (methyl β-D-glucopyranosiduronate)；methyl (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-octoxyoxane-2-carboxylate
• CAS: 148312-83-8
• 化学式: C₁₅H₂₈O₇
• 分子量: 320.383
• InChiKey: ACKBBJVQNULHIP-DKBOKBLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Methyl (octyl β-D-glucopyranosid)uronate 在 羟胺 作用下， 以 甲醇 、 水 为溶剂， 反应 16.0h， 以67%的产率得到octyl N-hydroxy-β-D-glucopyranosiduronamide
  参考文献：
  名称：

  Synthesis of sugar-based chelating surfactants for metal removal from wastewater

  摘要：

  Four chelating surfactants were synthesized in a few steps from octyl D-glucosides. Their main interfacial properties were determined, and their flotation properties were evaluated on a laboratory scale using Fe(III) as a model contaminant metal. The performance on metal extraction was mainly dependent on the complexing functional group, but the surfactant efficiency was also important. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.01.015
• 作为产物：
  描述：

  n-辛基-β-D-吡喃葡萄糖苷 在 盐酸 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 Carbonate buffer 、 水 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 Methyl (octyl β-D-glucopyranosid)uronate
  参考文献：
  名称：

  Electroorganic Synthesis 66: Selective Anodic Oxidation of Carbohydrates Mediated by TEMPO

  摘要：

  碳水化合物4-15在2,2,6,6-四甲基哌啶-1-氧自由基（TEMPO）的介导下进行阳极氧化。对初级羟基的选择性和完全反应在中等到优良的产率下生成相应的羧酸16-32。甲基α-d-葡萄糖苷以98%的产率转化为尿酸16。循环伏安法显示氧化是碱催化的，TEMPO+（2）对羟基的氧化是速率控制步骤。

  DOI：

  10.1055/s-1999-3464

文献信息

• Selective oxidation of monosaccharide derivatives to uronic acids
  作者：Nicola J. Davis、Sabine L. Flitsch

  DOI：10.1016/s0040-4039(00)77522-8

  日期：1993.2

  Pimary hydroxyl groups in partially protected monosaccharide derivatives were selectively oxidised to carboxylic acids using sodium hypochlorite in the presence of catalytic amounts of 2,2,6,6-tetramethyl-1-piperidinyl oxy, free radical (TEMPO). Acetal, benzyl and acyl-protection groups were unaffected during the oxidation reaction.

  在催化量的2,2,6,6-四甲基-1-哌啶基氧基自由基（TEMPO）存在下，使用次氯酸钠将部分保护的单糖衍生物中的羟基羟基选择性氧化为羧酸。缩醛，苄基和酰基保护基在氧化反应过程中不受影响。
• Electroorganic Synthesis 66: Selective Anodic Oxidation of Carbohydrates Mediated by TEMPO
  作者：Karsten Schnatbaum、Hans J. Schäfer

  DOI：10.1055/s-1999-3464

  日期：1999.5

  The carbohydrates 4-15 are anodically oxidized with 2,2,6,6-tetramethylpiperidin-1-oxyl (TEMPO) as mediator. Selective and complete reaction at the primary hydroxyl groups affords the corresponding carboxylic acid 16-32 in moderate to excellent yield. Methyl α-d-glucopyranoside is converted in 98% yield to the uronic acid 16. Cyclic voltammetry shows that the oxydation is base-catalyzed and the oxidation of the hydroxy group with TEMPO+ (2) is rate determining.

  碳水化合物4-15在2,2,6,6-四甲基哌啶-1-氧自由基（TEMPO）的介导下进行阳极氧化。对初级羟基的选择性和完全反应在中等到优良的产率下生成相应的羧酸16-32。甲基α-d-葡萄糖苷以98%的产率转化为尿酸16。循环伏安法显示氧化是碱催化的，TEMPO+（2）对羟基的氧化是速率控制步骤。
• Synthesis of sugar-based chelating surfactants for metal removal from wastewater
  作者：Nadège Ferlin、Diego Grassi、Carlos Ojeda、Mariano J.L. Castro、Eric Grand、Alicia Fernández Cirelli、José Kovensky

  DOI：10.1016/j.carres.2008.01.015

  日期：2008.4

  Four chelating surfactants were synthesized in a few steps from octyl D-glucosides. Their main interfacial properties were determined, and their flotation properties were evaluated on a laboratory scale using Fe(III) as a model contaminant metal. The performance on metal extraction was mainly dependent on the complexing functional group, but the surfactant efficiency was also important. (C) 2008 Elsevier Ltd. All rights reserved.