1,2-di-O-benzoyl-β-L-arabinopyranose | 359407-34-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2-di-O-benzoyl-β-L-arabinopyranose
• 英文别名: 1,2-di-O-benzoyl-α-L-arabinopyranose；[(2R,3R,4S,5S)-2-benzoyloxy-4,5-dihydroxyoxan-3-yl] benzoate
• CAS: 359407-34-4
• 化学式: C₁₉H₁₈O₇
• 分子量: 358.348
• InChiKey: AWNADEXWHXWRCO-YIOZNXECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,2-di-O-benzoyl-β-L-arabinopyranose 在 吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 60.5h， 生成 1,2,3-tri-O-benzoyl-4-S-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-4-thio-α-D-xylopyranose
  参考文献：
  名称：

  Stereoselective synthesis of thioxylooligosaccharides from S-glycosyl isothiourea precursors

  摘要：

  A stereoselective synthesis of thioxylo-di-, -tri-, -tetra- and -penta-saccharides from S-glycosyl isothiourea precursors is described. The synthesis was performed starting from 2,3,4-tri-O-acetyl-beta -D-xylopyranosyl isothiouronium bromide using a triethylamine promoted reaction with 1,2,3-tri-O-benzoyl-4-O-lrifluoromethanesuIphonyl-beta -L-arabinopyranose. The resulting 4-thioxylobisse was then converted into the corresponding isothiouroniurn bromide and used for the synthesis of 4,4 ' -dithioxylotriose. Higher homologues of the series and their alpha -methyl glycosides were also prepared. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00775-4
• 作为产物：
  描述：

  L-(+)-arabinose 在 吡啶 、 水 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.42h， 生成 1,2-di-O-benzoyl-β-L-arabinopyranose
  参考文献：
  名称：

  Stereoselective synthesis of thioxylooligosaccharides from S-glycosyl isothiourea precursors

  摘要：

  A stereoselective synthesis of thioxylo-di-, -tri-, -tetra- and -penta-saccharides from S-glycosyl isothiourea precursors is described. The synthesis was performed starting from 2,3,4-tri-O-acetyl-beta -D-xylopyranosyl isothiouronium bromide using a triethylamine promoted reaction with 1,2,3-tri-O-benzoyl-4-O-lrifluoromethanesuIphonyl-beta -L-arabinopyranose. The resulting 4-thioxylobisse was then converted into the corresponding isothiouroniurn bromide and used for the synthesis of 4,4 ' -dithioxylotriose. Higher homologues of the series and their alpha -methyl glycosides were also prepared. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00775-4

文献信息

• 4-Deoxy-4-fluoro-xyloside derivatives as inhibitors of glycosaminoglycan biosynthesis
  作者：Yasuhiro Tsuzuki、Thao Kim Nu Nguyen、Dinesh R. Garud、Balagurunathan Kuberan、Mamoru Koketsu

  DOI：10.1016/j.bmcl.2010.10.085

  日期：2010.12

  click chemistry for evaluating their potential utility as inhibitors of glycosaminoglycan biosynthesis. 2,3-Di-O-benzoyl-4-deoxy-4-fluoro-β-d-xylopyranosylazide, obtained from l-arabinopyranose by six steps, was treated with a wide variety of azide-reactive triple bond-containing hydrophobic agents in the presence of Cu2+ salt/ascorbic acid, a step known as click chemistry. After click chemistry, benzoylated

  使用点击化学制备了各种 4-脱氧-4-氟-木糖苷，以评估它们作为糖胺聚糖生物合成抑制剂的潜在效用。2,3- Di - O - benzoyl -4-deoxy-4-fluoro-β- d - xylopyranosylazide，通过六步从l-阿拉伯吡喃糖中获得，在Cu 2+的存在盐/抗坏血酸，这一步骤称为点击化学。单击化学后，苯甲酰化衍生物在 Zemplén 条件下脱保护以获得 4-脱氧-4-氟-木糖苷衍生物。然后使用 HPLC 在反相 C18 柱上分离 12 种衍生物的 α:β-异构体混合物，并评估所得 24 种 4-脱氧-4-氟-木糖苷抑制内皮细胞中糖胺聚糖生物合成的能力。我们确定了两种木糖苷衍生物，它们选择性地抑制硫酸乙酰肝素和硫酸软骨素/硫酸德曼生物合成而不影响细胞活力。这些新型衍生物可潜在地用于定义蛋白聚糖在模型生物中的生物学作用，也可用作治疗糖胺聚糖参与的各种人类疾病的治疗剂。
• Partially Acetylated or Benzoylated Arabinose Derivatives as Structurally Simple Organogelators: Effect of the Ester Protecting Group on Gel Properties
  作者：Rajkamal、Navendu P. Pathak、Tanmoy Halder、Shubhajit Dhara、Somnath Yadav

  DOI：10.1002/chem.201701669

  日期：2017.8.22

  interactions responsible for the self-assembly of gelators through IR spectroscopy and wide-angle X-ray scattering reveal that the primary interactions responsible are hydrogen bonds between the hydroxyl groups and ester C=O, which is absent in the solid state of the gelators. In addition, π interactions present in the 1,2-dibenzoylated derivative result in a more regular arrangement, which, in turn, leads

  糖基低分子量胶凝剂（LMWG）长期以来一直用于各种应用。在本文中，据报道结构简单的酯保护的阿拉伯糖苷是能够使芳族溶剂以及汽油和柴油胶凝的低分子量有机胶凝剂（LMOG）。通过详细的流变实验对凝胶的机械强度进行的研究表明，与1,1,2-二乙酰化凝胶剂相比，1,2-二苯甲酰化阿拉伯糖凝胶剂的凝胶具有更好的机械性能。根据详细的场发射SEM和AFM研究，可以根据前者形成直径比后者直径小的纤维的趋势来解释这些结果。通过红外光谱和广角X射线散射对负责胶凝剂自组装的相互作用的研究表明，负责相互作用的主要相互作用是羟基和酯C = O之间的氢键，而氢键在固态时不存在。胶凝剂。另外，存在于1，2-二苯甲酰化衍生物中的π相互作用导致更规则的排列，与1，2-二乙酰化的胶凝剂相比，其进而导致凝胶的更好的机械性能。
• Stereoselective synthesis of thioxylooligosaccharides from S-glycosyl isothiourea precursors
  作者：Farid M Ibatullin、Konstantin A Shabalin、Janne V Jänis、Stanislav I Selivanov

  DOI：10.1016/s0040-4039(01)00775-4

  日期：2001.7

  A stereoselective synthesis of thioxylo-di-, -tri-, -tetra- and -penta-saccharides from S-glycosyl isothiourea precursors is described. The synthesis was performed starting from 2,3,4-tri-O-acetyl-beta -D-xylopyranosyl isothiouronium bromide using a triethylamine promoted reaction with 1,2,3-tri-O-benzoyl-4-O-lrifluoromethanesuIphonyl-beta -L-arabinopyranose. The resulting 4-thioxylobisse was then converted into the corresponding isothiouroniurn bromide and used for the synthesis of 4,4 ' -dithioxylotriose. Higher homologues of the series and their alpha -methyl glycosides were also prepared. (C) 2001 Elsevier Science Ltd. All rights reserved.