methyl 2,3-di-O-benzoyl-6-O-benzyl-4-O-(2,3-di-O-benzoyl-6-O-benzyl-4-O-methylsulfonylethoxycarbonyl-β-D-glucopyranosyl)-α-D-glycopyranoside | 1154463-36-1

• 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-benzoyl-6-O-benzyl-4-O-(2,3-di-O-benzoyl-6-O-benzyl-4-O-methylsulfonylethoxycarbonyl-β-D-glucopyranosyl)-α-D-glycopyranoside
• 英文别名: [(2S,3R,4S,5R,6R)-3-benzoyloxy-5-[(2S,3R,4S,5R,6R)-3,4-dibenzoyloxy-5-(2-methylsulfonylethoxycarbonyloxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-2-methoxy-6-(phenylmethoxymethyl)oxan-4-yl] benzoate
• CAS: 1154463-36-1
• 化学式: C₅₉H₅₈O₁₉S
• 分子量: 1103.16
• InChiKey: SFNCHPSRKONMCA-UNRSOQPPSA-N

物化性质

• 沸点：
  1088.1±65.0 °C(predicted)
• 密度：
  1.38±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  79
• 可旋转键数：
  29
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  239
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-benzoyl-6-O-benzyl-4-O-(2,3-di-O-benzoyl-6-O-benzyl-4-O-methylsulfonylethoxycarbonyl-β-D-glucopyranosyl)-α-D-glycopyranoside 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 以100%的产率得到Bz(-2)[Bz(-3)][Bn(-6)]Glc(b1-4)[Bz(-2)][Bz(-3)][Bn(-6)]a-Glc1Me
  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：

  phenyl 2,3-di-O-benzoyl-6-O-benzyl-4-O-methylsulfonylethoxycarbonyl-1-thio-β-D-glucopyranoside 、 methyl 2,3-di-O-benzoyl-6-O-benzyl-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63%的产率得到methyl 2,3-di-O-benzoyl-6-O-benzyl-4-O-(2,3-di-O-benzoyl-6-O-benzyl-4-O-methylsulfonylethoxycarbonyl-β-D-glucopyranosyl)-α-D-glycopyranoside
  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