1,2,3,4-tetra-O-acetyl-6-O-(tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranose | 69685-27-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2,3,4-tetra-O-acetyl-6-O-(tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranose
• 英文别名: Octa-O-acetyl-6-O-α-D-mannopyranosyl-β-D-mannopyranose；O¹,O²,O³,O⁴-Tetraacetyl-O⁶-(tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranose；beta-D-Mannopyranose, 6-O-(2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosyl)-, tetraacetate；[(2R,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-[[(2R,3R,4S,5S,6S)-3,4,5,6-tetraacetyloxyoxan-2-yl]methoxy]oxan-2-yl]methyl acetate
• CAS: 69685-27-4
• 化学式: C₂₈H₃₈O₁₉
• 分子量: 678.598
• InChiKey: GNTLGGDVHFXGLI-HEOQLGAVSA-N

物化性质

• 沸点：
  661.4±55.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  47
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  238
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetra-O-acetyl-6-O-(tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranose 在 potassium disulphite 、 氢溴酸 、 potassium carbonate 作用下， 以 水 、 溶剂黄146 、 丙酮 为溶剂， 反应 9.5h， 生成 cinnamyl 2,3,4-tri-O-acetyl-6-O-(tetra-O-acetyl-α-D-mannopyranosyl)-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：

  β-D-mannopyranose pentaacetate 在 calcium sulfate 、 氢溴酸 、 碘 、 乙酸酐 、 溶剂黄146 、 silver(l) oxide 作用下， 生成 1,2,3,4-tetra-O-acetyl-6-O-(tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranose
  参考文献：
  名称：

  The Synthesis of Certain Disaccharide Acetates in the Mannose Series¹

  摘要：

  DOI：

  10.1021/ja01244a023

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