methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosiduronic acid | 156977-40-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosiduronic acid
• 英文别名: (2R,3S,4S,5R,6R)-5-acetyloxy-3-hydroxy-6-methoxy-4-phenylmethoxyoxane-2-carboxylic acid
• CAS: 156977-40-1
• 化学式: C₁₆H₂₀O₈
• 分子量: 340.33
• InChiKey: FCSHUSYEDSKERO-ZHMBSYLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosiduronic acid 在 叔丁基二甲硅基三氟甲磺酸酯 作用下， 以 甲苯 为溶剂， 生成 (2R,3S,4S,5R,6R)-5-Acetoxy-3-((2R,3R,4R,5S,6R)-6-acetoxymethyl-5-allyloxy-3-azido-4-benzyloxy-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：

  2,4,6-tri-O-acetyl-3-O-benzyl-L-idopyranosyl trichloroacetimidate 在 potassium bromide 吡啶 、 4-二甲氨基吡啶 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 camphor-10-sulfonic acid 、 三氟化硼乙醚 、 四丁基氯化铵 、 水 、 sodium methylate 、 2,2-二甲氧基丙烷 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 生成 methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosiduronic acid
  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

文献信息

• Davis, Nicola J.; Flitsch, Sabine L., Journal of the Chemical Society. Perkin transactions I, 1994, # 4, p. 359 - 368
  作者：Davis, Nicola J.、Flitsch, Sabine L.

  DOI：——

  日期：——