Dodecyl β-D-fructopyranoside | 154992-71-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Dodecyl β-D-fructopyranoside
• 英文别名: octyl β-D-fructopyranoside；(2R,3S,4R,5R)-2-dodecoxy-2-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 154992-71-9
• 化学式: C₁₈H₃₆O₆
• 分子量: 348.48
• InChiKey: FWPFWEPGJYUPNO-ZJPYXAASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-硝基苯甲酰氯 、 Dodecyl β-D-fructopyranoside 在 吡啶 作用下， 以80%的产率得到
  参考文献：
  名称：

  Decyl and dodecyl β-d-fructofuranosides

  摘要：

  Decyl and dodecyl beta-D-fructofuranosides are formed from D-fructose and catalysed by boron trifluoride alcoholates, in admixture with the corresponding alpha-D anomers and beta-D-pyranosides. These were separated by chromatography and each of the products was fully characterized by NMR spectroscopy and as tetrakis(p-nitrobenzoates). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00308-5
• 作为产物：
  描述：

  果糖 、 十二烷醇 在 三氯化铁 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以35%的产率得到Dodecyl β-D-fructopyranoside
  参考文献：
  名称：

  Ferrieres, Vincent; Benvegnu, Thierry; Lefeuvre, Martine, Journal of the Chemical Society. Perkin Transactions 2 (2001), 1999, # 5, p. 951 - 959

  摘要：

  DOI：

文献信息

• A new synthesis of O-glycosides from totally O-unprotected glycosyl donors
  作者：Vincent Ferrières、Jean-Noël Bertho、Daniel Plusquellec

  DOI：10.1016/0040-4039(95)00356-h

  日期：1995.4

  O-unprotected aldoses (D-glucose, D-galactose and D-mannose) and D-fructose in THF or 1,4-dioxane using anhydrous FeCl3 as promoter afforded either aldofuranosides 1, 3, 4 in good overall yields or exclusively β-D-fructopyranosides 7. Conversely α-D-aldopyranosides 2, 5 and 6 were obtained respectively from D-glucose, D-mannose and N-acetyl-D-glucosamine when the reactions were performed in the presence

  Ó的完全的-Glycosidation ø -unprotected醛糖（d葡萄糖，d半乳糖和d甘露糖），使用无水的FeCl在THF或1,4-二恶烷和D-果糖 href=https://www.molaid.com/MS_39881 target="_blank">果糖3作为助催化剂，得到任一aldofuranosides 1，3，4在良好的整体产量或仅β-D-果糖吡喃糖苷7。相反地，当在BF 3 .OEt 2的存在下在超声条件下进行反应时，分别从D-葡萄糖，D-甘露糖和N-乙酰基-D-葡萄糖胺获得α-D-醛糖吡喃二糖苷2、5和6。
• Mcm-41 Materials as Catalysts for the Synthesis of Alkyl Fructosides
  作者：A.M. van der Heijden、F. van Rantwijk、H. van Bekkum

  DOI：10.1080/07328309908543987

  日期：1999.1.1

  derivatives of fructose has lagged because no efficient synthesis was available. We have found that mesoporous materials of the MCM-41 type are active and selective catalysts for the alkylation of fructose. Quantitative yields were obtained in the reaction of fructose with lower alcohols, up to C4. For long chain alcohols yields were moderate but the alkyl fructopyranosides could be easily purified. The other

  糖的烷基化结合了两个主要可再生类别的基本特征，即。甘油三酸酯和碳水化合物，同时导致生物友好型表面活性剂和乳化剂。果糖的烷基化衍生物的开发滞后，因为没有有效的合成方法。我们发现MCM-41型中孔材料是果糖烷基化的活性和选择性催化剂。在果糖与低至C4的低级醇反应中获得定量收率。对于长链醇，产率中等，但是烷基果糖吡喃糖苷可以容易地纯化。其他异构体可以通过色谱法分离。
• Synthesis of Alkyl Fructosides Using Solid Acid Catalysts. Part I: Silica-Alumina Cracking Catalysts
  作者：A. T.J.W. de Goede、M. P.J. van Deurzen、I. G. van der Leij、A. M. van der Heijden、J. M.A. Baas、F. van Rantwijk、H. van Bekkum

  DOI：10.1080/07328309608005657

  日期：1996.4

  Silica-alumina cracking catalysts and acid clays efficiently catalyze the 2-O-alkylation of D-fructose with long chain alcohols. Under the conditions applied virtually no degradation of fructose is observed. L-Sorbose and the aldopentoses also undergo silica-alumina-catalyzed alkylation. The rate of conversion is related to the solubility of the monosaccharide and the stability of the intermediate oxocarbenium ion. Best results in fructose alkylation are obtained by applying a recirculation method with butyl fructoside as soluble intermediate.
• [EN] PROCESS FOR THE PREPARATION OF ALKYLGLYCOSIDES<br/>[FR] PROCEDE DE PREPARATION D'ALKYLGLYCOSIDES
  申请人：UNICHEMA CHEMIE B.V.

  公开号：WO1994009019A1

  公开（公告）日：1994-04-28

  (EN) A process for the preparation of alkylglycosides, preferably alkylfructosides, comprises reacting a monosaccharide or a short chain alkylglycoside with an alcohol, preferably a monohydric alcohol in the presence of an acid clay or an activated silia-alumina based craking catalyst. The alkylfructosides can be used as surfactants, emulsifiers, and the like.(FR) Un procédé de préparation d'alkylglycosides, de préférence d'alkylfructosides, consiste à faire réagir un monosaccharide ou un alkylglycoside à chaîne courte avec un alcool, de préférence un alcool monovalent, en présence d'une argile acide ou d'un catalyseur de craquage activé à base de silice-alumine. Ces alkylfructosides peuvent être utilisés comme tensio-actifs, émulsifiants et autres.