ethyl 2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-4-O-(4-methoxybenzyl)-1-thio-α-D-glucopyranoside | 1590421-93-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-4-O-(4-methoxybenzyl)-1-thio-α-D-glucopyranoside
• 英文别名: ethyl 2-[(2R,3R,4S,5R,6R)-6-ethylsulfanyl-3-[(4-methoxyphenyl)methoxy]-4,5-bis(phenylmethoxy)oxan-2-yl]ethanesulfonate
• CAS: 1590421-93-4
• 化学式: C₃₃H₄₂O₈S₂
• 分子量: 630.824
• InChiKey: NEHSZCLXMNSBSJ-IZDBAANZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  43
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  ethyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-glycopyranoside 在 吡啶 、 aluminum (III) chloride 、 lithium aluminium tetrahydride 、 正丁基锂 、 sodium methylate 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， -78.0~50.0 ℃ 、10.0 kPa 条件下， 反应 18.0h， 生成 ethyl 2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-4-O-(4-methoxybenzyl)-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.