3-(3-azido-4-benzyloxy-6-hydroxymethyl-5-methoxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-5-hydroxy-6-(3,4,5,6-tetrakis-benzyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester | 331233-74-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(3-azido-4-benzyloxy-6-hydroxymethyl-5-methoxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-5-hydroxy-6-(3,4,5,6-tetrakis-benzyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS: 331233-74-0
• 化学式: C₆₂H₆₉N₃O₁₆
• 分子量: 1112.24
• InChiKey: DOEOHPNJLZPREL-YCMQWWMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.93
• 重原子数：
  81.0
• 可旋转键数：
  27.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  226.28
• 氢给体数：
  2.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  3-(3-azido-4-benzyloxy-6-hydroxymethyl-5-methoxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-5-hydroxy-6-(3,4,5,6-tetrakis-benzyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 palladium on activated charcoal sodium hydroxide 、 pyridine-SO3 complex 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of oligomeric assemblies of a platelet-binding key disaccharide in heparin and their biological activities

  摘要：

  Heparin, highly sulfated glycosaminoglycan, binds to platelets. A key disaccharide unit in heparin was previously found to be responsible for the binding, and the Frequency of the disaccharide unit was important for the binding potency. A newly developed method based on the reductive amination was effectively applied to prepare structurally defined oligomeric assemblies possessing multiple units of the key disaccharide. From their platelet-binding activities measured by the competitive binding assay, the enhancement of the activity was clearly observed with increasing number of the key disaccharide. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01826-8
• 作为产物：
  描述：

  苄基 alpha-D-吡喃葡萄糖苷 在 吡啶 、 4-二甲氨基吡啶 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 sodium chlorite 、 sodium dihydrogenphosphate 、 tin(II) trifluoromethanesulfonate 、 camphor-10-sulfonic acid 、 叔丁基二甲硅基三氟甲磺酸酯 、 sodium methylate 、 sodium hydride 、 溶剂黄146 、 potassium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 、 叔丁醇 为溶剂， 生成 3-(3-azido-4-benzyloxy-6-hydroxymethyl-5-methoxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-5-hydroxy-6-(3,4,5,6-tetrakis-benzyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of oligomeric assemblies of a platelet-binding key disaccharide in heparin and their biological activities

  摘要：

  Heparin, highly sulfated glycosaminoglycan, binds to platelets. A key disaccharide unit in heparin was previously found to be responsible for the binding, and the Frequency of the disaccharide unit was important for the binding potency. A newly developed method based on the reductive amination was effectively applied to prepare structurally defined oligomeric assemblies possessing multiple units of the key disaccharide. From their platelet-binding activities measured by the competitive binding assay, the enhancement of the activity was clearly observed with increasing number of the key disaccharide. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01826-8

文献信息

• Sugar Chips immobilized with synthetic sulfated disaccharides of heparin/heparan sulfate partial structure
  作者：Masahiro Wakao、Akihiro Saito、Koh Ohishi、Yuko Kishimoto、Tomoaki Nishimura、Michael Sobel、Yasuo Suda

  DOI：10.1016/j.bmcl.2008.01.069

  日期：2008.4

  carbohydrate-protein interactions. Herein, we report syntheses of novel sulfated oligosaccharides possessing heparin and heparan sulfate partial disaccharide structures, their immobilization on gold-coated chips to prepare array-type Sugar Chips, and evaluation of binding potencies of proteins by surface plasmon resonance (SPR) imaging technology. Sulfated oligosaccharides were efficiently synthesized from glucosamine

  碳水化合物芯片技术在碳水化合物-蛋白质相互作用的高通量评估方面具有巨大潜力。在此，我们报告了具有肝素和硫酸乙酰肝素部分二糖结构的新型硫酸化寡糖的合成，将它们固定在镀金芯片上以制备阵列型糖芯片，以及通过表面等离子体共振 (SPR) 成像技术评估蛋白质的结合效力。硫酸化寡糖由葡糖胺和糖醛酸部分有效合成。然后使用先前报道的方法将合成的硫酸化寡糖轻松固定在镀金芯片上。这种分析方法的有效性在芯片和肝素结合蛋白之间的结合实验中得到证实，