O-(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)-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose | 100752-65-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(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)-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose
• CAS: 100752-65-6
• 化学式: C₄₇H₅₂N₆O₁₄
• 分子量: 924.962
• InChiKey: OJTIZUBDTWBEEK-WFZXPPBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  67.0
• 可旋转键数：
  20.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  256.58
• 氢给体数：
  2.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  O-(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)-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose 在 三甲基铵三氧化硫共聚物 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以74%的产率得到O-(2-azido-3,4-di-O-benzyl-2-deoxy-6-O-sulfo-α-D-glucopyranosyl)-(1->4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-1,6-anhydro-2-azido-2-deoxy-3-O-sulfo-β-D-glucopyranose, disodium 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：

  β-D-Glucopyranose, 1,6-anhydro-2-azido-4-O-[2,3-bis-O-(phenylmethyl)-4,6-O-(phenylmethylene)-β-D-glucopyranosyl]-2-deoxy-, 3-acetate 在 吡啶 、 chromium(VI) oxide 、 sodium hydroxide 、 4 A molecular sieve 、 硫脲 、 mercury dibromide 、 copper dichloride 作用下， 以 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 87.33h， 生成 O-(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)-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