methyl (2S)-2-methyl-3-(2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl)propanoate | 1118750-18-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2S)-2-methyl-3-(2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl)propanoate
• 英文别名: [(2R,3R,4R,5S,6R)-3,4,5-tribenzoyloxy-6-[(2S)-3-methoxy-2-methyl-3-oxopropyl]oxan-2-yl]methyl benzoate
• CAS: 1118750-18-7
• 化学式: C₃₉H₃₆O₁₁
• 分子量: 680.708
• InChiKey: ITMLYCXMDSHGSP-USUVQGPKSA-N

物化性质

• 熔点：
  169-170 °C
• 沸点：
  762.8±45.0 °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)：
  7.1
• 重原子数：
  50
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzoylglucosyl bromide 、 甲基丙烯酸甲酯 在 bis(1,5-cyclooctadiene)nickel (0) 、 2,4-二甲基-3-戊醇 、 2,6-二[(4R)-4-苯基-2-恶唑啉基]吡啶 、 锌 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 12.0h， 生成 methyl (2S)-2-methyl-3-(2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl)propanoate 、 methyl (2R)-2-methyl-3-(2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl)propanoate
  参考文献：
  名称：

  Sn-Free Ni-Catalyzed Reductive Coupling of Glycosyl Bromides with Activated Alkenes

  摘要：

  A mild, stereoselective method for the Ni-catalyzed synthesis of alpha-C-alkylglycosides is reported. This approach entails the reductive coupling of glycosyl bromides with activated alkenes at room temperature, with low alkene loading as an important feature. Diastereoselective coupling with 2-substituted acrylate derivatives was made possible through the use of 2,4-dimethyl-3-pentanol as a proton source.

  DOI：

  10.1021/ol8028737

文献信息

• Sn-Free Ni-Catalyzed Reductive Coupling of Glycosyl Bromides with Activated Alkenes
  作者：Hegui Gong、R. Stephen Andrews、Joseph L. Zuccarello、Stephen J. Lee、Michel R. Gagné

  DOI：10.1021/ol8028737

  日期：2009.2.19

  A mild, stereoselective method for the Ni-catalyzed synthesis of alpha-C-alkylglycosides is reported. This approach entails the reductive coupling of glycosyl bromides with activated alkenes at room temperature, with low alkene loading as an important feature. Diastereoselective coupling with 2-substituted acrylate derivatives was made possible through the use of 2,4-dimethyl-3-pentanol as a proton source.