O-(2,3-di-O-benzyl-β-D-glucopyranosyl)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose | 99541-24-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(2,3-di-O-benzyl-β-D-glucopyranosyl)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose
• 英文别名: O-(2,3-di-O-benzyl-β-D-glucopyranosyl)-(1→4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose；[(1R,2S,3R,4R,5R)-4-azido-2-[(2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3,4-bis(phenylmethoxy)oxan-2-yl]oxy-6,8-dioxabicyclo[3.2.1]octan-3-yl] acetate
• CAS: 99541-24-9
• 化学式: C₂₈H₃₃N₃O₁₀
• 分子量: 571.584
• InChiKey: LCYIGZOQJJVJLI-NSQYDQRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  137
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  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 palladium on activated charcoal 吡啶 、 chromium(VI) oxide 、 sodium hydroxide 、 4 A molecular sieve 、 氢气 、 三甲基铵三氧化硫共聚物 、 硫脲 、 mercury dibromide 作用下， 以 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 207.33h， 生成 O-(2-deoxy-2-sulfamido-6-O-sulfo-α-D-glucopyranosyl)-(1->4)-O-(β-D-glucopyranosyluronic acid)-(1->4)-1,6-anhydro-2-deoxy-2-sulfamido-3-O-sulfo-β-D-glucopyranose, pentasodium salt
  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-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6:2,3-dianhydro-β-D-mannopyranose 在 吡啶 、 sodium azide 、 ammonium chloride 、 copper dichloride 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.0h， 生成 O-(2,3-di-O-benzyl-β-D-glucopyranosyl)-(1->4)-3-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

• 一种磺达肝癸钠双糖中间体的制备方法
  申请人：江苏美迪克化学品有限公司

  公开号：CN110746471B

  公开（公告）日：2021-06-25

  本发明公开了一种磺达肝癸钠双糖中间体的制备方法，使1‑O‑取代基磺酰基‑2,3‑双‑O‑苄基‑4,6‑O‑亚苄基‑β‑D‑吡喃葡萄糖与1,6‑脱水‑2‑脱氧‑2‑叠氮基‑3‑O‑乙酰基‑β‑D‑吡喃葡萄糖反应可直接制成式I所示的磺达肝癸钠双糖中间体；同时以式I所示的磺达肝癸钠双糖中间体作为原料可以合成式IV所示的磺达肝癸钠双糖中间体；本发明方法简单、步骤少，收率高，且原子利用率高，三废少，适于工业化大规模生产。。
• [EN] AN EFFICIENT AND SCALABLE PROCESS FOR THE MANUFACTURE OF FONDAPARINUX SODIUM<br/>[FR] PROCÉDÉ EFFICACE ET EXTENSIBLE DE FABRICATION DE FONDAPARINUX SODIQUE
  申请人：RELIABLE BIOPHARMACEUTICAL CORP

  公开号：WO2013115817A1

  公开（公告）日：2013-08-08

  The present invention relates to a process for the synthesis of the Factor Xa anticoagulent Fondaparinux and related compounds. The invention relates, in addition, to efficient and scalable processes for the synthesis of various intermediates useful in the synthesis of Fondaparinux and related compounds.

  本发明涉及一种用于合成因子Xa抗凝剂Fondaparinux及相关化合物的过程。此外，该发明还涉及用于合成Fondaparinux及相关化合物的各种中间体的高效可扩展过程。
• EFFICIENT AND SCALABLE PROCESS FOR THE MANUFACTURE OF FONDAPARINUX SODIUM
  申请人：Patel Payal P.

  公开号：US20120116066A1

  公开（公告）日：2012-05-10

  The present invention relates to a process for the synthesis of the Factor Xa anticoagulent Fondaparinux and related compounds. The invention relates, in addition, to efficient and scalable processes for the synthesis of various intermediates useful in the synthesis of Fondaparinux and related compounds.

  本发明涉及一种合成因子Xa抗凝剂Fondaparinux及相关化合物的方法。此外，该发明还涉及一种高效且可扩展的合成过程，用于合成Fondaparinux及相关化合物中有用的各种中间体。
• 新工艺制备磺达肝癸钠中间体的双糖片段
  申请人：海门慧聚药业有限公司

  公开号：CN105622678A

  公开（公告）日：2016-06-01

  本发明涉及抗凝血药物磺达肝癸钠中间体双糖片段的制备新工艺。该工艺反应路线短，效率高，中间体易纯化，适合全保护肝素五糖商业业化生产。
• A facile preparation of uronates via selective oxidation with TEMPO/KBr/Ca(OCl)2 under aqueous conditions
  作者：Feng Lin、Wenjie Peng、Wen Xu、Xiuwen Han、Biao Yu

  DOI：10.1016/j.carres.2004.02.001

  日期：2004.4

  the TEMPO-mediated selective oxidation has the benefit of easier operation. A variety of partially protected saccharide derivatives (1a-l) have been successfully converted into the corresponding uronate derivatives, including disaccharide building blocks for GAG fragments and precursors to saponins. The beneficial effect of Aliquat 336 was also disclosed in the oxidation of certain substrates.

  在TEMPO介导的选择性氧化中添加固体Ca（OCl）（2）作为终端氧化剂具有易于操作的优点。多种部分受保护的糖衍生物（1a-1）已成功转化为相应的尿酸酯衍生物，包括GAG片段的二糖结构单元和皂苷的前体。在某些底物的氧化中也公开了Aliquat 336的有益作用。