(2R,3S,4S,5R,6R)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-6-acetoxymethyl-3-azido-4-benzyloxy-5-(2-oxo-ethoxy)-tetrahydro-pyran-2-yloxy]-4-benzyloxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester | 241129-85-1

• 分子结构分类: 有机化合物
• 英文名称: (2R,3S,4S,5R,6R)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-6-acetoxymethyl-3-azido-4-benzyloxy-5-(2-oxo-ethoxy)-tetrahydro-pyran-2-yloxy]-4-benzyloxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS: 241129-85-1
• 化学式: C₃₄H₄₁N₃O₁₄
• 分子量: 715.711
• InChiKey: MTJAEWPPTWUUSR-WKQLHBOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  51.0
• 可旋转键数：
  17.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  209.34
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R,6R)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-6-acetoxymethyl-3-azido-4-benzyloxy-5-(2-oxo-ethoxy)-tetrahydro-pyran-2-yloxy]-4-benzyloxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 在 sodium chlorite 、 sodium dihydrogenphosphate 作用下， 生成 (2R,3S,4S,5R,6R)-5-Acetoxy-3-((2R,3R,4R,5S,6R)-6-acetoxymethyl-3-azido-4-benzyloxy-5-carboxymethoxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and biological activity of oligomer-model compounds containing units of a key platelet-binding disaccharide of heparin

  摘要：

  A key disaccharide unit in heparin, O-(2-deoxy-2-sulfamido-6-O-sulfo-alpha-D-glucopyranosyl)-(1-->4)-2-O-sulfo-alpha-L-idopyranosyluronic acid, was previously found to be responsible for the binding interaction of heparin to platelets. A clustering effect to enhance the binding was found to be dependent on the number and frequency of the disaccharide units in a heparin molecule. To systematically examine the clustering effect, three oligomer-model compounds containing two or three units of the disaccharide were synthesized. These compounds inhibited (3)H-Iabelled heparin binding to human platelets more strongly than a compound containing only one unit of the disaccharide, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01084-9
• 作为产物：
  描述：

  4-O-Allyl-1,6-anhydro-2-O-tosyl-β-D-glucopyranose 在 哌啶 、 lead(IV) acetate 、 四氧化锇 、 叠氮化锂 、 叔丁基二甲硅基三氟甲磺酸酯 、 sodium methylate 、 sodium hydride 、 氯化铵 、 caesium carbonate 、 N-甲基吗啉氧化物 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 (2R,3S,4S,5R,6R)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-6-acetoxymethyl-3-azido-4-benzyloxy-5-(2-oxo-ethoxy)-tetrahydro-pyran-2-yloxy]-4-benzyloxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and biological activity of oligomer-model compounds containing units of a key platelet-binding disaccharide of heparin

  摘要：

  A key disaccharide unit in heparin, O-(2-deoxy-2-sulfamido-6-O-sulfo-alpha-D-glucopyranosyl)-(1-->4)-2-O-sulfo-alpha-L-idopyranosyluronic acid, was previously found to be responsible for the binding interaction of heparin to platelets. A clustering effect to enhance the binding was found to be dependent on the number and frequency of the disaccharide units in a heparin molecule. To systematically examine the clustering effect, three oligomer-model compounds containing two or three units of the disaccharide were synthesized. These compounds inhibited (3)H-Iabelled heparin binding to human platelets more strongly than a compound containing only one unit of the disaccharide, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01084-9