methyl (methyl (2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1⟶4)-(2-O-benzoyl-3-O-benzyl-α-L-idopyranosyl) uronate)-(1⟶4)-(methyl (2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1⟶4)-2-O-benzoyl-3-O-benzyl-α-L-idopyranoside) uronate | 1416152-74-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (methyl (2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1⟶4)-(2-O-benzoyl-3-O-benzyl-α-L-idopyranosyl) uronate)-(1⟶4)-(methyl (2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1⟶4)-2-O-benzoyl-3-O-benzyl-α-L-idopyranoside) uronate
• CAS: 1416152-74-3
• 化学式: C₈₃H₈₆N₆O₂₃
• 分子量: 1535.62
• InChiKey: HXQWXJWQIYZJLN-CRZAQFOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.98
• 重原子数：
  112.0
• 可旋转键数：
  35.0
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  352.17
• 氢给体数：
  1.0
• 氢受体数：
  25.0

反应信息

• 作为反应物：
  描述：

  methyl (methyl (2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1⟶4)-(2-O-benzoyl-3-O-benzyl-α-L-idopyranosyl) uronate)-(1⟶4)-(methyl (2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1⟶4)-2-O-benzoyl-3-O-benzyl-α-L-idopyranoside) uronate 、 methyl (2R,3S,4S,5R)-3-[(2R,3R,4R,5S,6R)-3-azido-4-phenylmethoxy-6-(phenylmethoxymethyl)-5-(2,2,2-trichloroacetyl)oxyoxan-2-yl]oxy-5-benzoyloxy-4-phenylmethoxy-6-phenylsulfanyloxane-2-carboxylate 在 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以94%的产率得到methyl (methyl (2-azido-3,6-di-O-benzyl-2-deoxy-4-O-trichloroacetyl-α-D-glucopyranosyl)-(1⟶4)-(2-O-benzoyl-3-O-benzyl-α-L-idopyranosyl) uronate)-(1⟶4)-(methyl (2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1⟶4)-(2-O-benzoyl-3-O-benzyl-α-L-idopyranosyl) uronate)-(1⟶4)-(methyl (2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1⟶4)-2-O-benzoyl-3-O-benzyl-α-L-idopyranoside) uronate
  参考文献：
  名称：

  First Gram-Scale Synthesis of a Heparin-Related Dodecasaccharide

  摘要：

  The first example of a gram-scale synthesis of a structurally defined, heparin-related dodecasaccharide is reported. An iterative 14-step process using an iduronate donor disaccharide delivers > 1g quantities of the dodecasaccharide sequence [GlcNS-IdoA2S](6)-OMe in 15% overall yield from the reducing terminal disaccharide, a 2 orders of magnitude increase in scale for access to synthetic heparanoid dodecasaccharide mimetics. The synthesis also delivers multigram amounts of the protected oligosaccharides from tetra- through to dodecasaccharide.

  DOI：

  10.1021/ol303112y
• 作为产物：
  描述：

  methyl (methyl (2-azido-3,6-di-O-benzyl-2-deoxy-4-O-trichloroacetyl-α-D-glucopyranosyl)-(1⟶4)-(2-O-benzoyl-3-O-benzyl-α-L-idopyranosyl) uronate)-(1⟶4)-(methyl (2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1⟶4)-2-O-benzoyl-3-O-benzyl-α-L-idopyranoside) uronate 在 吡啶 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以94%的产率得到methyl (methyl (2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1⟶4)-(2-O-benzoyl-3-O-benzyl-α-L-idopyranosyl) uronate)-(1⟶4)-(methyl (2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1⟶4)-2-O-benzoyl-3-O-benzyl-α-L-idopyranoside) uronate
  参考文献：
  名称：

  First Gram-Scale Synthesis of a Heparin-Related Dodecasaccharide

  摘要：

  The first example of a gram-scale synthesis of a structurally defined, heparin-related dodecasaccharide is reported. An iterative 14-step process using an iduronate donor disaccharide delivers > 1g quantities of the dodecasaccharide sequence [GlcNS-IdoA2S](6)-OMe in 15% overall yield from the reducing terminal disaccharide, a 2 orders of magnitude increase in scale for access to synthetic heparanoid dodecasaccharide mimetics. The synthesis also delivers multigram amounts of the protected oligosaccharides from tetra- through to dodecasaccharide.

  DOI：

  10.1021/ol303112y

文献信息

• [EN] PROCESS FOR THE PREPARATION OF POLYSACCHARIDES<br/>[FR] PROCÉDÉ DE PRÉPARATION DE POLYSACCHARIDES
  申请人：UNIV MANCHESTER

  公开号：WO2014140626A3

  公开（公告）日：2014-11-06