cinnamyl 2,3,4-tri-O-acetyl-6-O-(methylsulfonyl)-α-D-mannopyranoside | 101648-37-7

• 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-6-O-(methylsulfonyl)-α-D-mannopyranoside
• 英文别名: cinnamyl 2,3,4-tri-O-acetyl-6-O-methylsulfonyl-1-thio-α-D-mannopyranoside；[(2R,3R,4S,5S,6R)-4,5-diacetyloxy-2-(methylsulfonyloxymethyl)-6-[(E)-3-phenylprop-2-enyl]sulfanyloxan-3-yl] acetate
• CAS: 101648-37-7
• 化学式: C₂₂H₂₈O₁₀S₂
• 分子量: 516.59
• InChiKey: KVPNTKWEJRLFEU-UGJHDXOVSA-N

物化性质

• 沸点：
  644.4±55.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.93
• 重原子数：
  34.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  131.5
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  cinnamyl 2,3,4-tri-O-acetyl-6-O-(methylsulfonyl)-α-D-mannopyranoside 在 sodium azide 、 sodium methylate 、 sodium iodide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 cinnamyl 6-azido-6-deoxy-1-thio-α-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：

  2-S-(2,3,4-tri-O-acetyl-6-O-(methylsulfonyl)-α-D-mannopyranosyl)-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70%的产率得到cinnamyl 2,3,4-tri-O-acetyl-6-O-(methylsulfonyl)-α-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

文献信息

• Aralkyl and aralkenyl glycosides as inhibitors of antigen-specific
  申请人：Merck & Co., Inc.

  公开号：US04554349A1

  公开（公告）日：1985-11-19

  The invention disclosed herein relates to novel 1-deoxyglycosides, preferably 1-deoxy-D-mannopyranosides and 1-deoxy-L-rhamnopyranosides, having in the 1-position of the pyranose ring an aralkylthio/aralkenylthio, aralkyloxy/aralkenyloxy or aralkanoylamino/aralkenoylamino substituent; and to novel processes for preparing these 1-substituted-1-deoxyglycosides starting with the corresponding tetra-O-acetylglycopyranosyl bromide or amine. The 6-hydroxy group of 1-substituted-1 deoxyglycopyranosides can also be replaced by other functional groups. These aralkylthio/aralkenylthio, aralkyloxy/aralkenyloxy and aralkanoylamino/aralkenoylamino 1-deoxyglycosides are potent inhibitors of antigen-specific T-cell proliferation and are also useful as inhibitors of delayed-type hypersensitivity reactions.

  本发明涉及新颖的1-去氧糖苷，优选为1-去氧-D-甘露聚糖和1-去氧-L-鼠李糖苷，在吡喃糖环的1位具有芳基硫醚/芳基烯硫醚、芳基氧/芳基烯氧或芳基酰氨基/芳基烯酰氨基取代基；以及用于制备这些1-取代-1-去氧糖苷的新工艺，从相应的四-O-乙酰基糖吡喃糖溴化物或胺开始。1-取代-1-去氧糖苷的6-羟基也可以被其他功能基团取代。这些芳基硫醚/芳基烯硫醚、芳基氧/芳基烯氧和芳基酰氨基/芳基烯酰氨基1-去氧糖苷是抗原特异性T细胞增殖的有效抑制剂，也可用作延迟型超敏反应的抑制剂。
• US4554349A
  申请人：——

  公开号：US4554349A

  公开（公告）日：1985-11-19