ethyl 6-deoxy-6-C-(ethyl sulfonatomethyl)-2,3,4-tri-O-methyl-1-thio-α-D-glucopyranoside | 1590421-97-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 6-deoxy-6-C-(ethyl sulfonatomethyl)-2,3,4-tri-O-methyl-1-thio-α-D-glucopyranoside
• 英文别名: ethyl 2-[(2R,3R,4S,5R,6R)-6-ethylsulfanyl-3,4,5-trimethoxyoxan-2-yl]ethanesulfonate
• CAS: 1590421-97-8
• 化学式: C₁₄H₂₈O₇S₂
• 分子量: 372.504
• InChiKey: RNWBUVFBXSUVKW-RKQHYHRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  phenyl 2,3-di-O-acetyl-6-O-(2'-naphthyl)methyl-1-thio-β-D-glucopyranoside 、 ethyl 6-deoxy-6-C-(ethyl sulfonatomethyl)-2,3,4-tri-O-methyl-1-thio-α-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 四氢呋喃 、 甲苯 为溶剂， 反应 1.25h， 以89%的产率得到phenyl [6-deoxy-6-C-(ethyl sulfonatomethyl)-2,3,4-tri-O-methyl-α-D-glucopyranosyl]-(1→4)-2,3-di-O-acetyl-6-O-(2'-naphthyl)methyl-1-thio-β-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 2,3,4-tri-O-methyl-1-thio-α-D-glucopyranoside 在 吡啶 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 ethyl 6-deoxy-6-C-(ethyl sulfonatomethyl)-2,3,4-tri-O-methyl-1-thio-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

文献信息

• Large-scale synthesis of 6-deoxy-6-sulfonatomethyl glycosides and their application for novel synthesis of a heparinoid pentasaccharide trisulfonic acid of anticoagulant activity
  作者：Erika Mező、Mihály Herczeg、Dániel Eszenyi、Anikó Borbás

  DOI：10.1016/j.carres.2014.02.012

  日期：2014.3

  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.