tri-O-acetyl-S-ethoxythiocarbonyl-β-D-1-thio-6-deoxy-glucopyranose | 29581-34-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tri-O-acetyl-S-ethoxythiocarbonyl-β-D-1-thio-6-deoxy-glucopyranose
• 英文别名: Acetic acid (3R,4R,5S,6S)-4,5-diacetoxy-2-ethoxythiocarbonylsulfanyl-6-methyl-tetrahydro-pyran-3-yl ester
• CAS: 29581-34-8
• 化学式: C₁₅H₂₂O₈S₂
• 分子量: 394.467
• InChiKey: GWGOZUZKFRZUKB-KOIRDQTKSA-N

物化性质

• 沸点：
  456.9±45.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.58
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  tri-O-acetyl-S-ethoxythiocarbonyl-β-D-1-thio-6-deoxy-glucopyranose 在 sodium methylate 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 2.5h， 生成 cinnamyl 1-thio-β-L-rhamnopyranoside
  参考文献：
  名称：

  Inhibition of delayed hypersensitivity reactions by cinnamyl 1-thioglycosides

  摘要：

  Cinnamyl 1-thio-alpha-D-manno(and L-rhamno)pyranosides have good inhibitory effects in an antigen-specific T cell proliferation assay. The beta anomers are slightly less effective than the alpha anomers. The 6-substituted analogues of cinnamyl 1-thio-alpha-D-mannopyranoside such as 6-deoxy and 6-O-methyl derivatives also block macrophages in presenting the antigen to T cells. D-Mannose and L-rhamnose, when tested by themselves with no modifications, did not block at concentrations up to 1 mM. These cinnamyl 1-thioglycosides when given ip or po at 3-30 mg/kg to mice significantly inhibited the delayed type hypersensitivity reaction as measured by footpad swelling.

  DOI：

  10.1021/jm00387a021