2',3'-di-O-benzyl derivative of 1,6-anhydro-4',6'-O-benzylidenecellobiose | 99571-46-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2',3'-di-O-benzyl derivative of 1,6-anhydro-4',6'-O-benzylidenecellobiose
• CAS: 99571-46-7
• 化学式: C₃₃H₃₆O₁₀
• 分子量: 592.643
• InChiKey: PFOAZQIXCIRHAU-IGMCKYQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  43.0
• 可旋转键数：
  9.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  114.3
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2',3'-di-O-benzyl derivative of 1,6-anhydro-4',6'-O-benzylidenecellobiose 在 吡啶 、 sodium azide 、 ammonium chloride 、 sodium methylate 、 1-对甲基苯磺酰咪唑 、 copper dichloride 作用下， 以 乙醇 、 正己烷 、 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 46.5h， 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