Acetic acid (1R,2R,3S,4R,5R)-2-((2R,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-5-hydroxy-4-methoxy-tetrahydro-pyran-2-yloxy)-3-methoxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester | 226069-59-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (1R,2R,3S,4R,5R)-2-((2R,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-5-hydroxy-4-methoxy-tetrahydro-pyran-2-yloxy)-3-methoxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester
• 英文别名: [(2R,3R,4S,5R,6R)-5-acetyloxy-6-[[(1R,2R,3S,4R,5R)-4-acetyloxy-3-methoxy-6,8-dioxabicyclo[3.2.1]octan-2-yl]oxy]-3-hydroxy-4-methoxyoxan-2-yl]methyl acetate
• CAS: 226069-59-6
• 化学式: C₂₀H₃₀O₁₃
• 分子量: 478.45
• InChiKey: WCUYDGSSKQJHKP-XSVWGIRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  155
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  Acetic acid (1R,2R,3S,4R,5R)-2-((2R,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-5-hydroxy-4-methoxy-tetrahydro-pyran-2-yloxy)-3-methoxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester 在 ammonium cerium(IV) nitrate 、 4 A molecular sieve 、 叔丁基二甲硅基三氟甲磺酸酯 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 1.33h， 生成 [(2R,3R,4S,5R,6R)-5-acetyloxy-6-[(2R,3R,4S,5R,6S)-5-acetyloxy-6-[(2R,3R,4S,5R,6R)-5-acetyloxy-6-[[(1R,2R,3S,4R,5R)-4-acetyloxy-3-methoxy-6,8-dioxabicyclo[3.2.1]octan-2-yl]oxy]-2-(acetyloxymethyl)-4-methoxyoxan-3-yl]oxy-2-(acetyloxymethyl)-4-methoxyoxan-3-yl]oxy-3-hydroxy-4-methoxyoxan-2-yl]methyl acetate
  参考文献：
  名称：

  Synthetic oligosaccharides having various functional domains: Potent and potentially safe heparin mimetics

  摘要：

  A synthetic heptadecasaccharide, comprising an antithrombin III binding domain, a thrombin binding domain, and a neutral methylated hexasaccharide sequence, was obtained through a convergent synthesis. This compound displayed in vitro anticoagulant properties similar to that of standard heparin but, in contrast with heparin, escaped neutralization by platelet factor 4, a protein released by activated platelets. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00156-0
• 作为产物：
  描述：

  Acetic acid (2R,3R,4R,5R)-5-hydroxy-6-((1R,2R,3R,4R,5R)-4-hydroxy-3-methoxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-4-methoxy-3-(4-methoxy-phenoxy)-tetrahydro-pyran-2-ylmethyl ester 在 4-二甲氨基吡啶 、 ammonium cerium(IV) nitrate 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 Acetic acid (1R,2R,3S,4R,5R)-2-((2R,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-5-hydroxy-4-methoxy-tetrahydro-pyran-2-yloxy)-3-methoxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester
  参考文献：
  名称：

  Synthetic oligosaccharides having various functional domains: Potent and potentially safe heparin mimetics

  摘要：

  A synthetic heptadecasaccharide, comprising an antithrombin III binding domain, a thrombin binding domain, and a neutral methylated hexasaccharide sequence, was obtained through a convergent synthesis. This compound displayed in vitro anticoagulant properties similar to that of standard heparin but, in contrast with heparin, escaped neutralization by platelet factor 4, a protein released by activated platelets. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00156-0