methyl 2,3-di-O-benzyl-6-O-perfluorooctylpropylmethylsulfonylethoxycarbonyl-4-O-(2,3,6-tri-O-benzoyl-β-D-glucopyranosyl)-α-D-glucopyranoside | 1154463-80-5

• 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-6-O-perfluorooctylpropylmethylsulfonylethoxycarbonyl-4-O-(2,3,6-tri-O-benzoyl-β-D-glucopyranosyl)-α-D-glucopyranoside
• CAS: 1154463-80-5
• 化学式: C₆₂H₅₇F₁₇O₁₈S
• 分子量: 1445.16
• InChiKey: WMCQYGDVYHUKHI-AZBQSFFPSA-N

物化性质

• 沸点：
  1050.1±65.0 °C(predicted)
• 密度：
  1.50±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.67
• 重原子数：
  98.0
• 可旋转键数：
  31.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  224.18
• 氢给体数：
  1.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  4,6-O-di(tert-butyl)silylidene-2-deoxy-3-O-levulinoyl-2-trichloroacetamido-α-D-glucopyranosyl N-phenyl-2,2,2-trifluoroacetimidate 、 methyl 2,3-di-O-benzyl-6-O-perfluorooctylpropylmethylsulfonylethoxycarbonyl-4-O-(2,3,6-tri-O-benzoyl-β-D-glucopyranosyl)-α-D-glucopyranoside 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以78%的产率得到methyl 2,3-di-O-benzyl-6-O-perfluorooctylpropyllsulfonylethoxycarbonyl-4-O-[2,3,6-tri-O-benzoyl-4-O-{2-deoxy-4,6-di-tert-butylsilyl-3-O-levulinoyl-2-(N-trichloroacetyl)-amino-β-D-glucopyranosyl}-β-D-glucopyranosyl]-α-D-glucopyranoside
  参考文献：
  名称：

  Methylsulfonylethoxycarbonyl (Msc) and fluorous propylsulfonylethoxycarbonyl (FPsc) as hydroxy-protecting groups in carbohydrate chemistry

  摘要：

  The methylsulfonylethoxycarbonyl (Msc) group is presented as a non-lipophilic, base-labile, participating protecting group for carbohydrate alcohols. It can be introduced using Msc-Cl and pyridine and is readily cleaved via beta-elimination under mild basic conditions. Its fluorous counterpart, the perfluorooctyl propyl-sulfonylethoxycarbonyl (FPsc) group, is used in a 'light fluorous' trisaccharide synthesis sequence. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.146
• 作为产物：
  描述：

  methyl 2,3-di-O-benzyl-6-O-perfluorooctylpropylmethylsulfonylethoxycarbonyl-4-O-(2,3,6-tri-O-benzoyl-4-O-levulinoyl-β-D-glucopyranosyl)-α-D-glucopyranoside 在 一水合肼 、 溶剂黄146 作用下， 以 吡啶 为溶剂， 反应 0.08h， 以81%的产率得到methyl 2,3-di-O-benzyl-6-O-perfluorooctylpropylmethylsulfonylethoxycarbonyl-4-O-(2,3,6-tri-O-benzoyl-β-D-glucopyranosyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Methylsulfonylethoxycarbonyl (Msc) and fluorous propylsulfonylethoxycarbonyl (FPsc) as hydroxy-protecting groups in carbohydrate chemistry

  摘要：

  The methylsulfonylethoxycarbonyl (Msc) group is presented as a non-lipophilic, base-labile, participating protecting group for carbohydrate alcohols. It can be introduced using Msc-Cl and pyridine and is readily cleaved via beta-elimination under mild basic conditions. Its fluorous counterpart, the perfluorooctyl propyl-sulfonylethoxycarbonyl (FPsc) group, is used in a 'light fluorous' trisaccharide synthesis sequence. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.146