methyl [2,3-di-O-benzyl-4-O-(2'-naphthyl)methyl-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 | 1590422-08-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl [2,3-di-O-benzyl-4-O-(2'-naphthyl)methyl-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: 1590422-08-4
• 化学式: C₆₈H₈₂O₂₂S₂
• 分子量: 1315.52
• InChiKey: OQNZEHNBPXWFLG-BHPYYJHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.29
• 重原子数：
  92.0
• 可旋转键数：
  33.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  250.1
• 氢给体数：
  0.0
• 氢受体数：
  22.0

反应信息

• 作为反应物：
  描述：

  methyl [2,3-di-O-benzyl-4-O-(2'-naphthyl)methyl-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 0.5h， 以79%的产率得到methyl [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
• 作为产物：
  描述：

  ethyl 2-[(2R,3R,4S,5R,6R)-6-ethylsulfanyl-3-(naphthalen-2-ylmethoxy)-4,5-bis(phenylmethoxy)oxan-2-yl]ethanesulfonate 、 methyl [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 N-碘代丁二酰亚胺 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 3.5h， 以92%的产率得到methyl [2,3-di-O-benzyl-4-O-(2'-naphthyl)methyl-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