3-O-tert-butyldimethylsilyl-4,6-di-O-(tert-butyl)silanediyl-2-O-pivaloyl-α-D-mannopyranose | 316365-31-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-tert-butyldimethylsilyl-4,6-di-O-(tert-butyl)silanediyl-2-O-pivaloyl-α-D-mannopyranose
• 英文别名: 3-O-tertbutyldimethylsilyl-4,6-O-(di-tert-butylsilanediyl)-2-O-pivaloyl-α-D-mannopyranose
• CAS: 316365-31-8
• 化学式: C₂₅H₅₀O₇Si₂
• 分子量: 518.839
• InChiKey: AGRPJXQHSZZUQE-SLHNCBLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.51
• 重原子数：
  34.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  83.45
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3-O-tert-butyldimethylsilyl-4,6-di-O-(tert-butyl)silanediyl-2-O-pivaloyl-α-D-mannopyranose 在 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 甲苯 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 methyl 3-O-tert-butyldimethylsilyl-4,6-di-O-(tert-butyl)silanediyl-2-O-pivaloyl-α-D-mannopyranoside-(1->2)-3,4,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Formation of β-Glucosamine and β-Mannose Linkages Using Glycosyl Phosphates

  摘要：

  [GRAPHICS]Glycosyl phosphates were examined for their utility in the synthesis of challenging glycosidic linkages. beta -Glucosamine glycosides were formed preferentially and in good yield. beta -Mannosides were constructed in high overall yield with modest anomeric selectivity. Interesting solvent and conformational influences on the stereochemical outcome of the coupling reactions were observed.

  DOI：

  10.1021/ol006566+
• 作为产物：
  描述：

  di-tert-butylsilyl ditriflate 在 palladium on activated charcoal 咪唑 、 4-二甲氨基吡啶 、 氢气 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 35.5h， 生成 3-O-tert-butyldimethylsilyl-4,6-di-O-(tert-butyl)silanediyl-2-O-pivaloyl-α-D-mannopyranose
  参考文献：
  名称：

  Formation of β-Glucosamine and β-Mannose Linkages Using Glycosyl Phosphates

  摘要：

  [GRAPHICS]Glycosyl phosphates were examined for their utility in the synthesis of challenging glycosidic linkages. beta -Glucosamine glycosides were formed preferentially and in good yield. beta -Mannosides were constructed in high overall yield with modest anomeric selectivity. Interesting solvent and conformational influences on the stereochemical outcome of the coupling reactions were observed.

  DOI：

  10.1021/ol006566+