(2S,3S,4S,5R,6R)-6-((1R,2S,3R,4R,5R)-3-Acetoxy-4-azido-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-4,5-bis-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid | 100752-71-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S,5R,6R)-6-((1R,2S,3R,4R,5R)-3-Acetoxy-4-azido-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-4,5-bis-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid
• CAS: 100752-71-4
• 化学式: C₃₀H₃₂ClN₃O₁₂
• 分子量: 662.05
• InChiKey: OMVKRPWKVZTWIY-FSBLRMGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  46.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  194.04
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R,6R)-6-((1R,2S,3R,4R,5R)-3-Acetoxy-4-azido-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-4,5-bis-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid 在 硫脲 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 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
  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 、 chromium(VI) oxide 、 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 、 丙酮 为溶剂， 反应 46.33h， 生成 (2S,3S,4S,5R,6R)-6-((1R,2S,3R,4R,5R)-3-Acetoxy-4-azido-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-4,5-bis-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid
  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