ethyl 2,6-di-O-benzoyl-3-O-levulinoyl-4-O-[(RS)-1-methyl-1-(cyclopropyl)methyl]-1-thio-β-D-galactopyranoside | 512174-02-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,6-di-O-benzoyl-3-O-levulinoyl-4-O-[(RS)-1-methyl-1-(cyclopropyl)methyl]-1-thio-β-D-galactopyranoside
• CAS: 512174-02-6
• 化学式: C₃₂H₃₈O₉S
• 分子量: 598.714
• InChiKey: WGBLHLVQWGZDTC-SLSNKHTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.01
• 重原子数：
  42.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  114.43
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  ethyl 2,6-di-O-benzoyl-1-thio-β-D-galactopyranoside 在 silver trifluoromethanesulfonate 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 ethyl 2,6-di-O-benzoyl-3-O-levulinoyl-4-O-[(RS)-1-methyl-1-(cyclopropyl)methyl]-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Simplifying Oligosaccharide Synthesis:  Efficient Synthesis of Lactosamine and Siaylated Lactosamine Oligosaccharide Donors

  摘要：

  A practical sequence is described for converting D-glucosamine into peracetylated Gal(beta-1,4)-GlcNTroc(beta1-S)Ph and Neu5Ac(alpha-2,3)Gal(beta-1,4)GlcNTroc(beta1-S)Ph building blocks using a synthetic strategy based on chemoenzymatic oligosaccharide synthesis. The known trichloroethoxycarbonyl, N-Troc, protecting group was selected as a suitable protecting group for both enzymatic and chemical reaction conditions. These oligosaccharide building blocks proved effective donors for the,beta-selective glycosylation of the unreactive OH-3 of a polymeric PEG-bound acceptor and for the axial OH-2 of a mannose acceptor in good yields. The resulting complex oligosaccharides are useful for vaccine and pharmaceutical applications.

  DOI：

  10.1021/jo026569v