methyl [2,3,4-tri-O-methyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranosyl]-(1→4)-[2,3-di-O-acetyl-β-D-glucopyranosyl]-(1→4)-[2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranosyl]-(1→4)-[methyl (2-O-acetyl-3-O-methyl-α-L-idopyranosyl)uronate]-(1→4)-2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranoside | 1590422-11-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl [2,3,4-tri-O-methyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranosyl]-(1→4)-[2,3-di-O-acetyl-β-D-glucopyranosyl]-(1→4)-[2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranosyl]-(1→4)-[methyl (2-O-acetyl-3-O-methyl-α-L-idopyranosyl)uronate]-(1→4)-2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranoside
• CAS: 1590422-11-9
• 化学式: C₇₉H₁₁₀O₃₆S₃
• 分子量: 1731.92
• InChiKey: DIFMKUDWHBZZHA-RISVHALTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.43
• 重原子数：
  118.0
• 可旋转键数：
  45.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  421.68
• 氢给体数：
  1.0
• 氢受体数：
  36.0

反应信息

• 作为反应物：
  描述：

  methyl [2,3,4-tri-O-methyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranosyl]-(1→4)-[2,3-di-O-acetyl-β-D-glucopyranosyl]-(1→4)-[2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranosyl]-(1→4)-[methyl (2-O-acetyl-3-O-methyl-α-L-idopyranosyl)uronate]-(1→4)-2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranoside 在 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Large-scale synthesis of 6-deoxy-6-sulfonatomethyl glycosides and their application for novel synthesis of a heparinoid pentasaccharide trisulfonic acid of anticoagulant activity

  摘要：

  Multigram-scale syntheses of three 6-deoxy-6-sulfonatomethyl a-glucosides were accomplished via reactions of the corresponding primary triflate derivatives with the lithiated ethyl methanesulfonate. Chemoselective glycosylation reactions of different 6-C-sulfonatomethyl glucoside donors were studied. The sulfonic acid-containing building blocks were utilised in a novel [2+3] block synthesis of a trisulfonic acid isoster of the anticoagulant pentasaccharide idraparinux. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.02.012
• 作为产物：
  描述：

  methyl [2,3,4-tri-O-methyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranosyl]-(1→4)-[2,3-di-O-acetyl-6-O-(2'-naphthyl)methyl-β-D-glucopyranosyl]-(1→4)-[2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranosyl]-(1→4)-[methyl (2-O-acetyl-3-O-methyl-α-L-idopyranosyl)uronate]-(1→4)-2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranoside 在 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以84%的产率得到methyl [2,3,4-tri-O-methyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranosyl]-(1→4)-[2,3-di-O-acetyl-β-D-glucopyranosyl]-(1→4)-[2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranosyl]-(1→4)-[methyl (2-O-acetyl-3-O-methyl-α-L-idopyranosyl)uronate]-(1→4)-2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Large-scale synthesis of 6-deoxy-6-sulfonatomethyl glycosides and their application for novel synthesis of a heparinoid pentasaccharide trisulfonic acid of anticoagulant activity

  摘要：

  Multigram-scale syntheses of three 6-deoxy-6-sulfonatomethyl a-glucosides were accomplished via reactions of the corresponding primary triflate derivatives with the lithiated ethyl methanesulfonate. Chemoselective glycosylation reactions of different 6-C-sulfonatomethyl glucoside donors were studied. The sulfonic acid-containing building blocks were utilised in a novel [2+3] block synthesis of a trisulfonic acid isoster of the anticoagulant pentasaccharide idraparinux. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.02.012