methyl(benzyl 4-O-chloroacetyl-2,3-di-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside | 200712-71-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl(benzyl 4-O-chloroacetyl-2,3-di-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
• CAS: 200712-71-6
• 化学式: C₄₅H₅₁ClO₁₃
• 分子量: 835.345
• InChiKey: OYFDZMXBIJREOZ-LUWVSSPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.78
• 重原子数：
  59.0
• 可旋转键数：
  20.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  135.67
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  methyl(benzyl 4-O-chloroacetyl-2,3-di-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 在 吡啶 、 溶剂黄146 、 硫脲 、 三氟乙酸 作用下， 以 乙醇 为溶剂， 反应 4.5h， 生成 (benzyl 2,3-di-O-methyl-α-L-idopyranosyluronate)-(1->4)-1,3,6-tri-O-acetyl-2-O-benzyl-D-glucopyranose
  参考文献：
  名称：

  Assessment through chemical synthesis of the size of the heparin sequence involved in thrombin inhibition

  摘要：

  Deca- to eicosasaccharides having the generic structure methyl(sodium 2,3-di-O-methyl-4-O-sodium sulfonato-alpha-L-idopyranosyluronate)-(1 --> 4)-[(2,3,6-tri-O-sodium sulfonato-alpha-D-glucopyranosyl)-(1 --> 4)-(sodium 2,3-di-O-methyl-alpha-L-idopyranosyluronate) -( 1 --> 4)](n)-2,3,6-tri-O-sodium sulfonato-alpha-D-glucopyranoside have been synthesized from a single disaccharide precursor. All of them bind to and activate antithrombin. When n less than or equal to 6 only Factor Xa inhibition is observed, whereas when n > 6 Factor Xa and thrombin are both inhibited in the presence of antithrombin. These results indicate that, in heparin, the sequence involved in antithrombin-catalyzed thrombin inhibition is a pentadecaor a hexadecasaccharide. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00068-3
• 作为产物：
  描述：

  氯乙酸酐 、 Methyl (benzyl 2,3-di-O-methyl-α-L-idopyranosyluronate)(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以67%的产率得到methyl(benzyl 4-O-chloroacetyl-2,3-di-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Assessment through chemical synthesis of the size of the heparin sequence involved in thrombin inhibition

  摘要：

  Deca- to eicosasaccharides having the generic structure methyl(sodium 2,3-di-O-methyl-4-O-sodium sulfonato-alpha-L-idopyranosyluronate)-(1 --> 4)-[(2,3,6-tri-O-sodium sulfonato-alpha-D-glucopyranosyl)-(1 --> 4)-(sodium 2,3-di-O-methyl-alpha-L-idopyranosyluronate) -( 1 --> 4)](n)-2,3,6-tri-O-sodium sulfonato-alpha-D-glucopyranoside have been synthesized from a single disaccharide precursor. All of them bind to and activate antithrombin. When n less than or equal to 6 only Factor Xa inhibition is observed, whereas when n > 6 Factor Xa and thrombin are both inhibited in the presence of antithrombin. These results indicate that, in heparin, the sequence involved in antithrombin-catalyzed thrombin inhibition is a pentadecaor a hexadecasaccharide. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00068-3