1-octyl-β-D-xylopyranoside | 6743-68-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-octyl-β-D-xylopyranoside
• 英文别名: octyl β-D-xylopyranoside；n-octyl β-D-xyloside；n-octyl β-xyloside；n-octyl D-lyxopyranoside；octyl-β-D-xylopyranoside；Octyl-β-D-xylopyranosid；Octyl beta-D-xyloside；(2R,3R,4S,5R)-2-octoxyoxane-3,4,5-triol
• CAS: 6743-68-6
• 化学式: C₁₃H₂₆O₅
• 分子量: 262.346
• InChiKey: FEGZXXSLIVDCFL-YVECIDJPSA-N

物化性质

• 熔点：
  91-92 °C(Solv: acetone (67-64-1))
• 沸点：
  397.6±42.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-octyl-β-D-xylopyranoside 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 79.0h， 生成 Octyl 2,4-di-O-acetyl-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-xylopyranoside
  参考文献：
  名称：

  Regioselective Acetylations of Alkyl .beta.-D-Xylopyranosides by Use of Lipase PS in Organic Solvents and Application to the Chemoenzymic Synthesis of Oligosaccharides

  摘要：

  Aglycon structure and solvent can change the regioselectivity of the acetylation of alkyl beta-D-xylopyranosides, catalyzed by lipase PS. The acetylation of methyl beta-D-xylopyranoside (3) in acetonitrile gave the 3,4-diacetate 4 exclusively, whereas the reaction of octyl beta-D-xylopyranoside (5) gave a mixture of 2,4- and 3,4-diacetates (6 and 7) in 1.0:1.3 and 3.6:1.0 ratios, in acetonitrile and hexane, respectively. The effect of several solvents on the selectivity in the monoacetylation of 5 was studied. The 2-monoacetate 8 was preferentially formed over the 3- and 4-monoacetates (9 and 10) in hydrophobic solvents. High yields of partially acetylated xylose derivatives were obtained, which were used in the syntheses of a disaccharide showing liquid crystal properties, an intermediate for the synthesis of proteoglycan fragments, and a trisaccharide potential inhibitor of plant growth.

  DOI：

  10.1021/jo00102a029
• 作为产物：
  描述：

  tetra-O-acetyl-β-D-xylopyranose 在 氢溴酸 、 碘 、 sodium methylate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 1-octyl-β-D-xylopyranoside
  参考文献：
  名称：

  碳氢化合物和碳氟化合物烷基 β-D-吡喃木糖苷表面活性剂的合成、热性能和细胞毒性评估。

  摘要：

  烷基 β-d-吡喃木糖苷是一种高表面活性、可生物降解的表面活性剂，可从半纤维素制备，可用作药物、洗涤剂、农用化学品和个人护理产品。为了进一步了解它们的结构-性质和构效关系，本研究合成了一系列碳氢化合物（-C（6）H（13）到-C（16）H（33））和碳氟化合物（-（CH (2))(2)C(6)F(13)) 烷基 β-d-吡喃木糖苷分四步从 d-木糖通过酰化或苯甲酰化、溴化、Koenigs-Knorr 反应和水解得到，苯甲酰基保护基团给出与 Koenigs-Knorr 反应中的酰基相比，产率更高。所有烷基β-d-吡喃木糖苷均形成热致液晶。固体结晶相到液晶相的相变随着疏水尾的长度线性增加。具有疏水尾部 8 的烷基 β-d-吡喃木糖苷的清除点接近恒定，但对于己基 β-d-吡喃木糖苷发生在显着较低的温度下。短链和长链烷基 β-d-吡喃木糖苷在浓度低于其水溶性极限时不显示细胞毒性。由于细胞凋亡，具有中等链长的碳氢化合物和碳氟化合物烷基

  DOI：

  10.1016/j.carres.2011.11.020

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。
• Ionic liquid promoted atom economic glycosylation under Lewis acid catalysis
  作者：Jacques Augé、Gwenaëlle Sizun

  DOI：10.1039/b904692e

  日期：——

  Straightforward glycosylation of various alcohols with unprotected and non-activated monosaccharides were performed under scandium triflate catalysis. Rate and yield of glycosylation were highly improved when using 1-butyl-3-methylimidazolium trifluoromethanesulfonate as a green solvent. This ionic liquid was allowed to be recycled at least three times without loss of activity. The possibility of drastically reducing the amounts of catalyst (down to 1 mol%) and aglycone (down to 1 equiv) when performing the reaction in ionic liquid opens new perspectives in O-glycosylation, as a direct coupling between an aglycone and free sugars.

  在钪三氟甲磺酸盐催化下，对各种醇与未保护和非活化的单糖进行了直接的糖苷化反应。当使用1-丁基-3-甲基咪唑三氟甲磺酸盐作为绿色溶剂时，糖苷化的反应速率和产率得到了显著提高。该离子液体可至少回收使用三次而不会失去活性。在离子液体中进行反应时，可以显著减少催化剂的用量（低至1 mol%）和糖苷的用量（低至1当量），这为O-糖苷化的直接耦合提供了新的前景，能够在糖苷和游离糖之间实现直接连接。
• Surfactants of biological origin: The role of Mo(VI) and microwaves in the synthesis of xylan-based non-ionic surfactants
  作者：Zuzana Hricovíniová

  DOI：10.1016/j.carbpol.2016.02.070

  日期：2016.6

  glycosylation of unprotected d-xylose and d-lyxose, obtained after tandem Mo(VI)-catalyzed xylan hydrolysis-epimerization reaction, provides alkyl xylosides and lyxosides in short reaction times. A homologous series of amphiphilic alkyl pentosides varying in chain structure (C8-C14) was prepared in very good yields (38-73%). A new catalytic approach using the reusable heterogeneous PMoA/SiO2 catalyst provides

  微波辅助的磷钼酸（PMoA）催化的，未经保护的d-木糖和d-木糖的串联糖基化反应，是在Mo（VI）催化的木聚糖水解-表观电子化反应后获得的，可在较短的反应时间内提供烷基木糖苷和lyxosides。以非常好的收率（38-73％）制备了一系列在链结构上不同的两亲烷基戊糖苷的同源序列（C8-C14）。使用可重复使用的非均相PMoA / SiO2催化剂的新催化方法在产量，环境安全性，操作简便性方面均具有优势，从而为合理利用半纤维素生物质开辟了新视野。
• Boronic Acids as Phase-Transfer Reagents for Fischer Glycosidations in Low-Polarity Solvents
  作者：Sanjay Manhas、Mark S. Taylor

  DOI：10.1021/acs.joc.7b01880

  日期：2017.11.3

  Protocols employing phenylboronic acid as a phase-transfer reagent for Fischer glycosidations in low-polarity organic solvents are described. In addition to providing rate acceleration, the formation of a substrate-derived boronic ester alters the course of the reaction by selective promotion of a furanoside- or pyranoside-selective pathway. Computational modeling of the relative energies of the glycoside-derived

  描述了在低极性有机溶剂中使用苯基硼酸作为相转移试剂进行费歇尔糖基化的方案。除了提供速率加速以外，底物衍生的硼酸酯的形成还通过选择性促进呋喃糖苷或吡喃糖苷选择性途径来改变反应过程。糖苷衍生的硼酸酯相对能量的计算模型提供的结果在质量上与呋喃糖苷与吡喃糖苷产品的分布相吻合。作为这些反应的直接产物获得的硼酸酯用作合成官能化糖苷的受保护中间体。特定的二醇基团与硼酸的络合也使得碳水化合物混合物的选择性转化成为可能。
• Konstantinovic; Petrovic; Spasojevic, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 7, p. 614 - 618
  作者：Konstantinovic、Petrovic、Spasojevic、Mojsilovic

  DOI：——

  日期：——