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.
• Non-Amphiphilic Carbohydrate Liquid Crystals Containing an Intact Monosaccharide Moiety
  作者：E. Smits、J. B.F.N. Engberts、R. M. Kellogg、H. A. Van Doren

  DOI：10.1080/10587259508038691

  日期：1995.2

  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.
• Rational design of reversible inhibitors for trehalose 6-phosphate phosphatases
  作者：Chunliang Liu、Debra Dunaway-Mariano、Patrick S. Mariano

  DOI：10.1016/j.ejmech.2017.02.001

  日期：2017.3

  ortholog is 5.3 ± 0.6 μM, 70-fold smaller than the substrate Michaelis constant. The binding specificity of 9a was demonstrated using several representative sugar phosphate phosphatases from the HAD enzyme superfamily, the T6PP protein fold family of origin. Lastly, correlations drawn between T6PP active site structure, inhibitor structure and inhibitor binding affinity suggest that the aryl d-glucopyranoside

  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