((2R,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-(ethylthio)-3-((4-methoxybenzyl)oxy)tetrahydro-2H-pyran-2-yl)methyl trifluoromethanesulfonate | 1590422-14-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((2R,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-(ethylthio)-3-((4-methoxybenzyl)oxy)tetrahydro-2H-pyran-2-yl)methyl trifluoromethanesulfonate
• CAS: 1590422-14-2
• 化学式: C₃₁H₃₅F₃O₈S₂
• 分子量: 656.741
• InChiKey: IFNDZNOBMSPELS-CMPUJJQDSA-N

物化性质

• 沸点：
  685.4±55.0 °C(predicted)
• 密度：
  1.34±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  44.0
• 可旋转键数：
  15.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  ((2R,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-(ethylthio)-3-((4-methoxybenzyl)oxy)tetrahydro-2H-pyran-2-yl)methyl trifluoromethanesulfonate 、 甲磺酸乙酯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以5.6 g的产率得到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
• 作为产物：
  描述：

  (2R,3R,4S,5S,6R)-2-Ethylsulfanyl-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 在 吡啶 、 aluminum (III) chloride 、 lithium aluminium tetrahydride 、 sodium hydride 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， -10.0~50.0 ℃ 、10.0 kPa 条件下， 反应 17.5h， 生成 ((2R,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-(ethylthio)-3-((4-methoxybenzyl)oxy)tetrahydro-2H-pyran-2-yl)methyl trifluoromethanesulfonate
  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