(2R,3S,4S,5R,6R)-6-[(2R,3S,4R,5R,6R)-6-[2-[[(2R)-2,3-bis(phenylmethoxycarbonylamino)propanoyl]amino]ethyl]-4-hydroxy-2-(hydroxymethyl)-5-methoxyoxan-3-yl]oxy-3-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4S,5S,6S)-6-carboxy-5-[(2R,3R,4S,5R,6R)-6-(hydroxymethyl)-3,4,5-trimethoxyoxan-2-yl]oxy-3,4-dimethoxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5-dimethoxyoxane-2-carboxylic acid | 511511-44-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4S,5R,6R)-6-[(2R,3S,4R,5R,6R)-6-[2-[[(2R)-2,3-bis(phenylmethoxycarbonylamino)propanoyl]amino]ethyl]-4-hydroxy-2-(hydroxymethyl)-5-methoxyoxan-3-yl]oxy-3-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4S,5S,6S)-6-carboxy-5-[(2R,3R,4S,5R,6R)-6-(hydroxymethyl)-3,4,5-trimethoxyoxan-2-yl]oxy-3,4-dimethoxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5-dimethoxyoxane-2-carboxylic acid
• CAS: 511511-44-7
• 化学式: C₅₉H₈₇N₃O₃₂
• 分子量: 1350.34
• InChiKey: FFYBTVXQIMQSPN-KUBPNRPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  94
• 可旋转键数：
  34
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  459
• 氢给体数：
  11
• 氢受体数：
  32

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R,6R)-6-[(2R,3S,4R,5R,6R)-6-[2-[[(2R)-2,3-bis(phenylmethoxycarbonylamino)propanoyl]amino]ethyl]-4-hydroxy-2-(hydroxymethyl)-5-methoxyoxan-3-yl]oxy-3-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4S,5S,6S)-6-carboxy-5-[(2R,3R,4S,5R,6R)-6-(hydroxymethyl)-3,4,5-trimethoxyoxan-2-yl]oxy-3,4-dimethoxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5-dimethoxyoxane-2-carboxylic acid 在 三乙胺三氧化硫 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以100%的产率得到
  参考文献：
  名称：

  Probing the Heparin−Antithrombin III Interaction Using Synthetic Pentasaccharides Bearing Positively Charged Groups

  摘要：

  Four heparin pentasaccharides bearing either one (i.e. 3b and 4b) or two (i.e. 3c and 4c) positively charged amino groups at the reducing end have been synthesized and evaluated for their antithrombin III mediated anti-Xa activity. The positively charged groups were introduced to interact specifically with the negatively charged amino acid residues Glu113 and Asp 117 of antithrombin III, which are located in the heparin binding. site in close proximity to the reducing end of the saccharide. It turned out that the target compounds 3b,c and 4b,c exhibited relatively low anti-Xa activities, indicating unfavorable interactions between the new pentasaccharides and antithrombin III rather than the anticipated enhancement of association. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).

  DOI：

  10.1002/1099-0690(200212)2002:23<3954::aid-ejoc3954>3.0.co;2-2
• 作为产物：
  描述：

  在 N-甲基吗啉 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 (2R,3S,4S,5R,6R)-6-[(2R,3S,4R,5R,6R)-6-[2-[[(2R)-2,3-bis(phenylmethoxycarbonylamino)propanoyl]amino]ethyl]-4-hydroxy-2-(hydroxymethyl)-5-methoxyoxan-3-yl]oxy-3-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4S,5S,6S)-6-carboxy-5-[(2R,3R,4S,5R,6R)-6-(hydroxymethyl)-3,4,5-trimethoxyoxan-2-yl]oxy-3,4-dimethoxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5-dimethoxyoxane-2-carboxylic acid
  参考文献：
  名称：

  Probing the Heparin−Antithrombin III Interaction Using Synthetic Pentasaccharides Bearing Positively Charged Groups

  摘要：

  Four heparin pentasaccharides bearing either one (i.e. 3b and 4b) or two (i.e. 3c and 4c) positively charged amino groups at the reducing end have been synthesized and evaluated for their antithrombin III mediated anti-Xa activity. The positively charged groups were introduced to interact specifically with the negatively charged amino acid residues Glu113 and Asp 117 of antithrombin III, which are located in the heparin binding. site in close proximity to the reducing end of the saccharide. It turned out that the target compounds 3b,c and 4b,c exhibited relatively low anti-Xa activities, indicating unfavorable interactions between the new pentasaccharides and antithrombin III rather than the anticipated enhancement of association. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).

  DOI：

  10.1002/1099-0690(200212)2002:23<3954::aid-ejoc3954>3.0.co;2-2

文献信息

• Probing the Heparin−Antithrombin III Interaction Using Synthetic Pentasaccharides Bearing Positively Charged Groups
  作者：Jeroen D. C. Codée、Gijsbert A. van der Marel、Constant A. A. van Boeckel、Jacques H. van Boom

  DOI：10.1002/1099-0690(200212)2002:23<3954::aid-ejoc3954>3.0.co;2-2

  日期：2002.12

  Four heparin pentasaccharides bearing either one (i.e. 3b and 4b) or two (i.e. 3c and 4c) positively charged amino groups at the reducing end have been synthesized and evaluated for their antithrombin III mediated anti-Xa activity. The positively charged groups were introduced to interact specifically with the negatively charged amino acid residues Glu113 and Asp 117 of antithrombin III, which are located in the heparin binding. site in close proximity to the reducing end of the saccharide. It turned out that the target compounds 3b,c and 4b,c exhibited relatively low anti-Xa activities, indicating unfavorable interactions between the new pentasaccharides and antithrombin III rather than the anticipated enhancement of association. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).