methyl 2,3-di-O-benzyl-4-O-levulinoyl-6-O-methylsulfonylethoxycarbonyl-α-D-glucopyranoside | 1154463-28-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: methyl 2,3-di-O-benzyl-4-O-levulinoyl-6-O-methylsulfonylethoxycarbonyl-α-D-glucopyranoside
• CAS: 1154463-28-1
• 化学式: C₃₀H₃₈O₁₂S
• 分子量: 622.691
• InChiKey: MCMIJGGRESGMHR-RIAYOEEMSA-N

物化性质

• 沸点：
  749.0±60.0 °C(predicted)
• 密度：
  1.30±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  43.0
• 可旋转键数：
  16.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  149.96
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-benzyl-4-O-levulinoyl-6-O-methylsulfonylethoxycarbonyl-α-D-glucopyranoside 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.42h， 以95%的产率得到methyl 2,3-di-O-benzyl-4-O-levulinoyl-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-methylsulfonylethoxycarbonyl-α-D-glucopyranoside 、 乙酰丙酸 在 4-二甲氨基吡啶 、 ethylene dichloride hydrochloride 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以89%的产率得到methyl 2,3-di-O-benzyl-4-O-levulinoyl-6-O-methylsulfonylethoxycarbonyl-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