Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-2-carbamimidoylsulfanyl-6-methoxymethyl-tetrahydro-pyran-3-yl ester; hydrobromide | 101648-55-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-2-carbamimidoylsulfanyl-6-methoxymethyl-tetrahydro-pyran-3-yl ester; hydrobromide
• 英文别名: [(2R,3R,4S,5S,6R)-4,5-diacetyloxy-6-carbamimidoylsulfanyl-2-(methoxymethyl)oxan-3-yl] acetate;hydrobromide
• CAS: 101648-55-9
• 化学式: BrH*C₁₄H₂₂N₂O₈S
• 分子量: 459.315
• InChiKey: CERPCVPDVXUSRE-RLBMKGCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.36
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  173
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-2-carbamimidoylsulfanyl-6-methoxymethyl-tetrahydro-pyran-3-yl ester; hydrobromide 在 potassium disulphite 、 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 5.0h， 生成 cinnamyl 6-O-methyl-1-thio-β-D-mannopyranoside
  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：

  1,2,3,4-四-O-乙酰基Β-D吡喃甘露糖 在 三氟化硼乙醚 、 氢溴酸 作用下， 以 二氯甲烷 、 溶剂黄146 、 丙酮 为溶剂， 反应 8.0h， 生成 Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-2-carbamimidoylsulfanyl-6-methoxymethyl-tetrahydro-pyran-3-yl ester; hydrobromide
  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

文献信息

• US4554349A
  申请人：——

  公开号：US4554349A

  公开（公告）日：1985-11-19