O-(6-O-acetyl-2-azide-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1→4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1→4)-2-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose | 99541-27-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(6-O-acetyl-2-azide-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1→4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1→4)-2-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose
• 英文别名: O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose
• CAS: 99541-27-2
• 化学式: C₅₁H₅₆N₆O₁₆
• 分子量: 1009.04
• InChiKey: ZNKBYQIZKKPZDJ-YZJIZUTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.33
• 重原子数：
  73.0
• 可旋转键数：
  22.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  268.72
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  O-(6-O-acetyl-2-azide-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1→4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1→4)-2-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 三甲基铵三氧化硫共聚物 作用下， 以 甲醇 、 乙醚 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 118.0h， 生成
  参考文献：
  名称：

  Synthesis, from cellobiose, of a trisaccharide closely related to the GlcNAc→GlcA→GlcN segment of the anti-thrombin-binding sequence of heparin

  摘要：

  O-(2-Deoxy-2-sulfamido-6-O-sulfo-alpha-D-glucopyranosyl)-(1----4)- O-(beta-D- glucopyranosyluronic acid)-(1----4)-1,6-anhydro-2-deoxy-2-sulfamido-6-O-sulfo-beta-D-gl ucopyranose pentasodium salt (14) was synthesized as a heparin-related oligosaccharide. The glycosyl acceptor (derived from cellobiose) and a glycosyl donor, 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-alpha-D-glucopyranosyl bromide, were coupled in the presence of mercuric bromide and molecular sieves 4A to afford a 69% yield of fully protected trisaccharide, namely, O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-alpha-D-glucopyranosyl)-(1 ----4)- O-(methyl 2,3-di-O-benzyl-beta-D-glucopyranosyluronate)-(1----4)-3-O-acetyl- 1,6-anhydro-2 - azido-2-deoxy-beta-D-glucopyranose (10), which was converted into the partially sulfated trisaccharide 14. Compound 10 also underwent acetolysis to afford the glycosyl acetate, for further elongation of the glycosyl chain.

  DOI：

  10.1016/s0008-6215(00)90458-0
• 作为产物：
  描述：

  O-(2,3-di-O-benzyl-β-D-glucopyranosyl)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose 在 吡啶 、 chromium(VI) oxide 、 4 A molecular sieve 、 硫脲 、 mercury dibromide 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 83.33h， 生成 O-(6-O-acetyl-2-azide-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1→4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1→4)-2-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose
  参考文献：
  名称：

  Synthesis, from cellobiose, of a trisaccharide closely related to the GlcNAc→GlcA→GlcN segment of the anti-thrombin-binding sequence of heparin

  摘要：

  O-(2-Deoxy-2-sulfamido-6-O-sulfo-alpha-D-glucopyranosyl)-(1----4)- O-(beta-D- glucopyranosyluronic acid)-(1----4)-1,6-anhydro-2-deoxy-2-sulfamido-6-O-sulfo-beta-D-gl ucopyranose pentasodium salt (14) was synthesized as a heparin-related oligosaccharide. The glycosyl acceptor (derived from cellobiose) and a glycosyl donor, 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-alpha-D-glucopyranosyl bromide, were coupled in the presence of mercuric bromide and molecular sieves 4A to afford a 69% yield of fully protected trisaccharide, namely, O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-alpha-D-glucopyranosyl)-(1 ----4)- O-(methyl 2,3-di-O-benzyl-beta-D-glucopyranosyluronate)-(1----4)-3-O-acetyl- 1,6-anhydro-2 - azido-2-deoxy-beta-D-glucopyranose (10), which was converted into the partially sulfated trisaccharide 14. Compound 10 also underwent acetolysis to afford the glycosyl acetate, for further elongation of the glycosyl chain.

  DOI：

  10.1016/s0008-6215(00)90458-0

文献信息

• Total Synthesis of Anticoagulant Pentasaccharide Fondaparinux
  作者：Tiehai Li、Hui Ye、Xuefeng Cao、Jiajia Wang、Yonghui Liu、Lifei Zhou、Qiang Liu、Wenjun Wang、Jie Shen、Wei Zhao、Peng Wang

  DOI：10.1002/cmdc.201400019

  日期：2014.5

  The anticoagulant pentasaccharide fondaparinux was synthesized using an improved and optimized synthetic strategy including a convergent [3+2] coupling approach, orthogonal protecting groups and various glycosyl donors. The new methods of glycosylation were also used for controlling the stereochemical configuration and improving the yield of the glycosylation. In addition, HPLC and NMR methods to monitor

  抗凝五糖磺达肝素是使用改进和优化的合成策略合成的，包括收敛的[3 + 2]偶联方法，正交保护基和各种糖基供体。糖基化的新方法也用于控制立体化学构型和提高糖基化的产率。另外，采用HPLC和NMR方法监测磺达肝素的全合成过程。这项工作在相关文献的基础上为磺达肝素的合成和分析提供了详尽的阐述，并为肝素样低聚糖的合成提供了丰富的信息。
• 磺达肝癸钠五糖中间体及其制备方法
  申请人：上海艾康睿医药科技有限公司

  公开号：CN103601766B

  公开（公告）日：2016-04-20

  本发明涉及一种化学制备技术领域的磺达肝癸钠五糖中间体及其制备方法，具体是磺达肝癸钠五糖中间体的制备方法，包括磺达肝癸钠的三糖中间体，以及相关的制备方法。本发明设计了一条新的合成路线来制备磺达肝癸钠五糖中间体。这条路线具有反应温和、反应选择性好、可控性强、操作难度低，非常有利于工业化生产的实现；并且本发明的路线成本低廉，使得本发明的方法能够满足大规模工业化生产的要求。
• PROCESS FOR THE PRODUCTION OF FONDAPARINUX SODIUM
  申请人：Scinopharm Taiwan, LTD.

  公开号：US20150031866A1

  公开（公告）日：2015-01-29

  The present invention provides improved processes of preparing Fondaparinux sodium comprising converting a compound of formula ABCDE4 to Fondaparinux sodium at a reaction pH of no more than about 9.0. In some embodiments, the intermediates for the synthesis of Fondaparinux sodium, are also provided.

  本发明提供了改进的法那普利钠制备过程，包括将化合物ABCDE4转化为法那普利钠，在反应pH值不超过约9.0的条件下进行。在某些实施例中，还提供了用于合成法那普利钠的中间体。
• [EN] PROCESS FOR THE PRODUCTION OF FONDAPARINUX SODIUM<br/>[FR] PROCÉDÉ DE PRODUCTION DE FONDAPARINUX SODIUM
  申请人：SCINOPHARM TAIWAN LTD

  公开号：WO2015011519A1

  公开（公告）日：2015-01-29

  The present invention provides improved processes of preparing Fondaparinux sodium comprising converting a compound of formula ABCDE4 to Fondaparinux sodium at a reaction pH of no more than about 9.0. In some embodiments, the intermediates for the synthesis of Fondaparinux sodium, are also provided.

  本发明提供了改进的制备Fondaparinux钠的过程，包括将式ABCDE4的化合物转化为Fondaparinux钠，反应pH不超过约9.0。在某些实施例中，还提供了合成Fondaparinux钠的中间体。
• [EN] PROCESS FOR THE PRODUCTION OF FONDAPARINUX SODIUM<br/>[FR] PROCÉDÉ DE PRODUCTION DE SODIUM DE FONDAPARINUX
  申请人：SCINOPHARM TAIWAN LTD

  公开号：WO2015011517A1

  公开（公告）日：2015-01-29

  The present invention provides novel processes for the preparation of Fondaparinux sodium by using the compound of formula ABC5. In some embodiments, the intermediates for the synthesis of Fondaparinux sodium, are also provided.

  本发明提供了一种使用公式ABC5化合物制备Fondaparinux钠的新型工艺。在某些实施例中，还提供了合成Fondaparinux钠的中间体。