methyl 2,3-di-O-benzyl-6-O-methylsulfonylethoxycarbonyl-α-D-glucopyranoside | 1154463-25-8

• 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-methylsulfonylethoxycarbonyl-α-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-3-hydroxy-6-methoxy-4,5-bis(phenylmethoxy)oxan-2-yl]methyl 2-methylsulfonylethyl carbonate
• CAS: 1154463-25-8
• 化学式: C₂₅H₃₂O₁₀S
• 分子量: 524.589
• InChiKey: LYWJGSSRRGHSQK-SJSRKZJXSA-N

物化性质

• 沸点：
  690.3±55.0 °C(predicted)
• 密度：
  1.32±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  36
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  phenyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside 、 methyl 2,3-di-O-benzyl-6-O-methylsulfonylethoxycarbonyl-α-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以64%的产率得到methyl 2,3-di-O-benzyl-6-O-methylsulfonylethoxycarbonyl-4-O-(2,3,4,6-tetra-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
• 作为产物：
  描述：

  2-甲基磺酰基氯甲酸乙酯 、 2,3-二-o-苄基-alpha-d-吡喃葡萄糖苷甲酯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以90%的产率得到methyl 2,3-di-O-benzyl-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