octyl (2,3,4,6-tetra-O-acetyl)-α-D-galactopyranoside | 102935-49-9

• 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: octyl (2,3,4,6-tetra-O-acetyl)-α-D-galactopyranoside
• 英文别名: [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-octoxyoxan-2-yl]methyl acetate
• CAS: 102935-49-9
• 化学式: C₂₂H₃₆O₁₀
• 分子量: 460.522
• InChiKey: RNGLREVZONTJLS-CTWRKMMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  32
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  octyl (2,3,4,6-tetra-O-acetyl)-α-D-galactopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以98%的产率得到octyl α-D-galactopyranoside
  参考文献：
  名称：

  探索超分子环境中糖构型的含义：通过ITC和NMR光谱比较六个辛基糖苷胶束†

  摘要：

  合成了一系列甘露糖基-半乳糖基和葡萄糖基辛基α-和β-糖苷，并将其用于水中均胶束和杂胶束的形成。临界胶束浓度（cmc），消解的热力学量以及糖胶束的流体力学半径通过等温滴定量热法（ITC）和扩散NMR研究确定。这项工作的目的是确定对于相应糖苷的超分子特征，端基异构体构型以及在糖环上差向异构化的重要性。提出了新的糖苷结构预测，以促进这方面的结构-性质关系的解释。

  DOI：

  10.1039/c4md00122b
• 作为产物：
  描述：

  octyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 在 六甲基二硅烷 、 碘 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以60%的产率得到octyl (2,3,4,6-tetra-O-acetyl)-α-D-galactopyranoside
  参考文献：
  名称：

  碘-六甲基乙硅烷（HMDS）介导的过乙酰化1,2-反式连接的烷基和芳基糖苷的异构化

  摘要：

  已经发现在HMDS存在下用碘处理过乙酰化的烷基和芳基1，2-反式-糖苷会导致异构化，从而导致形成相应的1，2-顺式-糖苷。在具有短烷基链长的糖苷配基的烷基糖苷的情况下，观察到完全糖化为α-糖苷，而对于那些具有较长链长的糖苷，发现该过程是不完全的。这些观察已被机械地解释了。

  DOI：

  10.1016/j.carres.2010.02.012

文献信息

• Site-Selective, Copper-Mediated <i>O</i>-Arylation of Carbohydrate Derivatives
  作者：Victoria Dimakos、Graham E. Garrett、Mark S. Taylor

  DOI：10.1021/jacs.7b09420

  日期：2017.11.1

  site-selective, copper-promoted couplings of boronic acids with carbohydrate derivatives. These reactions generate sugar-derived aryl ethers, a structural class that is challenging to generate by other means and has not previously been accessed in a site-selective fashion. Experimental evidence and computational modeling suggest that the formation of a sugar-derived boronic ester intermediate is crucial to the

  糖衍生物中羟基的位点选择性功能化是碳水化合物合成中的主要挑战。实现这一目标的方法将为获得新的糖衍生化学构建块提供有效途径，并将促进复杂寡糖的制备或后期修饰，以用于糖生物学研究和药物发现。在这里，我们描述了硼酸与碳水化合物衍生物的位点选择性、铜促进偶联。这些反应生成糖衍生的芳基醚，这是一种结构类别，很难通过其他方式生成，并且以前没有以位点选择性方式进行访问。实验证据和计算模型表明，糖衍生的硼酸酯中间体的形成对这些过程的选择性至关重要，加速相邻羟基的芳基化。结果证明了糖与硼化合物的相互作用如何与过渡金属催化结合以实现新的化学反应性。
• 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。
• n-Octyl (Thio)glycosides as Potential Cryoprotectants: Glass Transition Behaviour, Membrane Permeability, and Ice Recrystallization Inhibition Studies
  作者：Rekha Raju、Theresa Merl、Madeleine K. Adam、Emiliyan Staykov、Robert N. Ben、Gary Bryant、Brendan L. Wilkinson

  DOI：10.1071/ch19159

  日期：——

  and varying anomeric configuration were synthesized and evaluated for glass transition behaviour, membrane permeability, and ice recrystallization inhibition (IRI) activity. Of these, n-octyl β-d-glucopyranoside (2β) exhibited a high glass transition temperatures (Tg), both as a neat sample and 20 wt-% aqueous solution. Membrane permeability studies of this compound revealed cellular uptake to concentrations

  合成了一系列八个带有d-葡萄糖或d-半乳糖构型和不同端基构型的正辛基（硫）糖苷（1α，β–4α，β），并评估了其玻璃化转变性能，膜渗透性和冰重结晶抑制（IRI）活性。其中，正辛基β- d-吡喃葡萄糖苷（2β）的玻璃化转变温度高（T g），既是纯净样品又是20 wt％的水溶液。该化合物的膜通透性研究表明，细胞吸收至与抑制细胞内冰形成有关的浓度，因此为进一步的生物物理和冷冻保存研究提供了有希望的潜在候选者。还评估了化合物作为冰的重结晶抑制剂。但是，新测试的化合物未发现可检测的活性。
• Konstantinović; Dimitrijević; Radulović, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 3, p. 598 - 603
  作者：Konstantinović、Dimitrijević、Radulović

  DOI：——

  日期：——
• A reevaluation of the epimeric and anomeric relationship of glucosides and galactosides in thermotropic liquid crystal self-assemblies
  作者：Rauzah Hashim、Seyed M. Mirzadeh、Thorsten Heidelberg、Hiroyuki Minamikawa、Tanaka Yoshiaki、Akhiko Sugimura

  DOI：10.1016/j.carres.2011.10.032

  日期：2011.12

  Anomers and epimers alpha- and beta-gluco and -galactosides are expected to behave differently. However, recent results on a series of Guerbet glycosides have indicated similar liquid crystal clearing temperatures for pure p-glucosides and the corresponding alpha-galactosides. This observation has led to speculation on similarities in the self-assembly interactions between the two systems, attributed to the trans-configuration of the 4-OH group and the hydrophobic aglycon. Previous simulations on related bilayers systems support this hypothesis, by relating this clearing transition temperature to intralayer (sugar-sugar) hydrogen bonding. In order to confirm the hypothesis, the comparison was expanded to include the cis-configurated pair, that is, alpha-gluco/beta-galactoside. A set of alpha-configurated Guerbet glucosides as well as octyl alpha-galactoside were prepared and their thermotropic phase behavior studied. The data obtained enabled a complete comparison of the isomers of interest. While the results in general are in line with a pairing of the stereo-isomers according to the indicated cis/trans-configuration, differences within the pairs can be explained based on the direction of hydrogen bonds from a simple modeling study. (C) 2011 Elsevier Ltd. All rights reserved.