cinnamyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside | 101648-48-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cinnamyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside
• CAS: 101648-48-0；106929-84-4
• 化学式: C₂₁H₂₆O₇S
• 分子量: 422.499
• InChiKey: SXASAUKWEUYIDO-ULQQQNLGSA-N

物化性质

• 沸点：
  518.9±50.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  88.13
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  cinnamyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以60%的产率得到cinnamyl 1-thio-β-L-fucopyranoside
  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
• 作为产物：
  描述：

  2-S-(2,3,4-tri-O-acetyl-β-L-fucopyranosyl)-2-thiopseudourea hydrobromide 、 Cinnamyl bromide 在 potassium disulphite 、 potassium carbonate 作用下， 以 水 、 丙酮 为溶剂， 反应 0.5h， 以58%的产率得到cinnamyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside
  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