octyl β-D-fructopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: octyl β-D-fructopyranoside
• 英文别名: (2R,3S,4R,5R)-2-(hydroxymethyl)-2-octoxyoxane-3,4,5-triol
• 化学式: C₁₄H₂₈O₆
• 分子量: 292.373
• InChiKey: GCACDCMZOROIFU-YIYPIFLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  9
• 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：

  、 octyl β-D-fructopyranoside 以 1,2-二氯乙烷 为溶剂， 生成
  参考文献：
  名称：

  基于手性BINOL的吡啶-酚类大环化合物对天然糖的对映体固液萃取

  摘要：

  开发了一种手性的含1,1'-联-2-萘酚（BINOL）的吡啶-乙炔-苯酚大环和吡啶-BINOL交替大环用于对映体糖的识别。在固液提取天然糖的过程中，这些大环化合物从d / l-果糖，d / l-葡萄糖和d / l-甘露糖的外消旋混合物的每一种中选择性地提取一种对映异构体到亲脂性溶剂中。这是第一个实例，其中用人工宿主分子对映选择性地提取天然糖，尤其是重要的己糖。

  DOI：

  10.1021/acs.orglett.9b01980
• 作为产物：
  描述：

  果糖 、 辛醇 在 silica-alumina cracking catalyst HA-HPV 作用下， 70.0 ℃ 、2.0 kPa 条件下， 反应 4.0h， 生成 octyl β-D-fructopyranoside
  参考文献：
  名称：

  Synthesis of Alkyl Fructosides Using Solid Acid Catalysts. Part I: Silica-Alumina Cracking Catalysts

  摘要：

  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.

  DOI：

  10.1080/07328309608005657

文献信息

• Polyvinyl trisulfonate ethylamine based solid acid catalyst for the efficient glycosylation of sugars under solvent free conditions
  作者：Avinash A. Chaugule、Amol R. Jadhav、Hern Kim

  DOI：10.1039/c5ra20300g

  日期：——

  We have synthesized Brønsted solid acid catalysts which exhibited effective catalytic activity for acid catalyzed glycosylation reactions.

  我们合成了Brønsted固体酸催化剂，对酸催化的糖基化反应表现出有效的催化活性。
• 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。
• Saccharide Recognition by a Three‐Arm‐Shaped Host Having Preorganized Three‐Dimensional Hydrogen‐Bonding Sites
  作者：Yuki Ohishi、Kentaro Masuda、Kazuki Kudo、Hajime Abe、Masahiko Inouye

  DOI：10.1002/chem.202004147

  日期：2021.1.7

  was readily prepared compared to a cage‐shaped analogue. This host associated with lipophilic glycosides to form chiral complexes, and the association constants were sufficiently high as to be comparable to those of the cage‐shaped analogue. Furthermore, this host extracted native monosaccharides into a lipophilic solvent.

  通常，由于三维预组织的氢键结合位点，糖的笼形宿主可以与客体分子牢固结合。然而，由于大环化步骤的产率低，通常很难制备笼状分子。在这里，我们报告一个具有吡啶-乙炔-苯酚单元的三臂形分子，作为一种具有预先组织的三维氢键位点的新型主体。与笼形类似物相比，这种三臂形宿主易于准备。该宿主与亲脂性糖苷结合形成手性复合物，缔合常数足够高，足以与笼形类似物的缔合常数相比。此外，该宿主将天然单糖提取到亲脂性溶剂中。
• Verhart, Cor G.J.; Fransen, Carel T.M.; Zwanenburg, Binne, Recueil des Travaux Chimiques des Pays-Bas, 1996, vol. 115, # 2, p. 133 - 139
  作者：Verhart, Cor G.J.、Fransen, Carel T.M.、Zwanenburg, Binne、Chittenden, Gordon J.F.

  DOI：——

  日期：——