p-octylphenyl-β-D-glucopyranoside | 132337-95-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-octylphenyl-β-D-glucopyranoside
• 英文别名: 4-n-octylphenyl β-D-glucopyranoside；(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-octylphenoxy)oxane-3,4,5-triol
• CAS: 132337-95-2
• 化学式: C₂₀H₃₂O₆
• 分子量: 368.47
• InChiKey: URIRUWFJHLGWQP-OUUBHVDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  p-octylphenyl-β-D-glucopyranoside 在 三氧化硫吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以42%的产率得到4-n-octylphenyl β-D-glucopyranoside-6-sulfate
  参考文献：
  名称：

  海藻糖6-磷酸磷酸酶可逆抑制剂的合理设计

  摘要：

  在某些生物中，环境压力触发了海藻糖生物合成，海藻糖生物合成由海藻糖6-磷酸合酶和海藻糖6-磷酸磷酸酶（T6PP）共同催化。T6PP催化将海藻糖6-磷酸酯（T6P）水解为海藻糖和无机磷酸酯，是开发抗菌，抗真菌和抗蠕虫药的有希望的目标。在这里，我们报告设计，合成和评估的芳基d-吡喃葡萄糖苷6硫酸盐的库，以用作小分子T6PP抑制剂的原型。稳态动力学技术用于测量一组源自病原体马来亚布鲁氏菌（Brugia malayi），猪scar虫（Ascaris suum），多种结构上不同的T6PP直系同源物的抑制常数（K i）。结核分枝杆菌，博伊氏志贺氏菌和鼠伤寒沙门氏菌。发现这些T6PP直系同源物中最活跃的抑制剂4-正辛基苯基α - d-吡喃葡萄糖苷6-硫酸盐（9a）的结合亲和力在低微摩尔范围内。与马来西亚芽孢杆菌T6PP直系同源物的9a的K i为5.3±0.6μM，比底物Michaelis常数小70倍。9

  DOI：

  10.1016/j.ejmech.2017.02.001
• 作为产物：
  描述：

  4-Octylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 三甲胺 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 生成 p-octylphenyl-β-D-glucopyranoside
  参考文献：
  名称：

  Non-Amphiphilic Carbohydrate Liquid Crystals Containing an Intact Monosaccharide Moiety

  摘要：

  A chiral rigid moiety which forms the basis of a new class of non-amphiphilic carbohydrate liquid crystals has been developed. This moiety contains a fully intact glucopyranose ring embedded in a trans-decalin structure. The original carbohydrate is substituted so that only two hydroxyl groups are left, resulting in derivatives with reduced hydrophilicity. The substituents R and X-R' on the 4,6-O-ylidene beta-D-glucopyranoside are in the equatorial position and can be varied extensively, using straightforward synthetic procedures. Investigations as to the requirements for R and X-R' for inducing liquid-crystalline behavior have shown that at least one of the substituents should contain a large, polarizable aromatic moiety. An aromatic Schiff base fulfils this requirement.

  DOI：

  10.1080/10587259508038691

文献信息

• Organofluorine compounds and fluorinating agents
  作者：Dirk Schwäbisch、Ralf Miethchen

  DOI：10.1016/s0022-1139(02)00310-x

  日期：2003.3

  The perfluorohexyl-aryl-thioethers 3 and 4, building blocks for the synthesis of the chiral target mesogens 12-15, were prepared by dithionite-mediated S-perfluoroalkylation of the p-substituted thiophenols 1 and 2. The phenolic HO- group of 3 was O-glucosylated with pentaacetyl-D-glucopyranose to 5 followed by deacetylation forming the tetrol 6 and by acetalizing with 4-(4-perfluorohexylsulfanylbenzoyloxy)-benzaldehyde-dimethylacetal (8) generating the dihydroxy-intermediate 9. The latter contains two perfluorohexylthio chains. Alternatively, the dimethylacetal 8 was linked to p-octylphenyl-beta-(D)-glucopyranoside (10) giving the mixed octyl/perfluorohexyl substituted p-octylphenyl-4,6-O-[4'-(4"-perfluorohexylsulfanyl)-benzoyloxy]-benzylidene-beta-(D)-glucopyranoside (11). Compound 8 was obtained via esterification of 4 with p-hydroxy-benzaldehyde to 4-(4-perfluorohexylsulfanyl-benzoyloxy)-benzaldehyde (7). Finally, the diols 9 and 11 were dehydroxylated to 12 and 13 followed by hydrogenation yielding 14 and 15, respectively. Tetrol 6, diols 9, 11 and the non-amphiphilic compounds 7, 12-15 are thermotropic liquid crystals. (C) 2002 Elsevier Science B.V. All rights reserved.