cyclohexyl 2,3-di-O-benzyl-4,6-bis-O-(tert-butyldimethylsilyl)-β-D-mannopyranoside | 160204-43-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cyclohexyl 2,3-di-O-benzyl-4,6-bis-O-(tert-butyldimethylsilyl)-β-D-mannopyranoside
• CAS: 160204-43-3
• 化学式: C₃₈H₆₂O₆Si₂
• 分子量: 671.078
• InChiKey: PPKLKXYFVUAKHV-DQROVBKRSA-N

物化性质

• 沸点：
  637.246±55.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.041±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.64
• 重原子数：
  46.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  丙酮酸乙酯 、 cyclohexyl 2,3-di-O-benzyl-4,6-bis-O-(tert-butyldimethylsilyl)-β-D-mannopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 cyclohexyl 2,3-di-O-benzyl-5,6-O-<(1-ethoxycarbonyl)ethylidene>-D-mannopyranoside 、 cyclohexyl 2,3-di-O-benzyl-4,6-O-<(R)-(1-ethoxycarbonyl)ethylidene>-α-D-mannopyranoside 、 cyclohexyl 2,3-di-O-benzyl-4,6-O-<(S)-(1-ethoxycarbonyl)ethylidene>-α-D-mannopyranoside
  参考文献：
  名称：

  Convenient synthesis of pyruvate acetals of carbohydrates by coupling of trialkylsilylated diols and pyruvates

  摘要：

  Hexopyranoside diols, mainly 4,6-diols with alpha-gluco, beta-gluco, alpha-galacto, beta-galacto, and alpha-manno configurations could be converted effectively (40 - 74% yields), to the corresponding pyruvate acetals by the coupling of the O-trialkylsilylated, namely, O-TBDMS and/or O-TMS diols, and ethyl pyruvate in the presence of TMSOTf at temperatures between -30 degrees C and +3 degrees C. In the case of the beta-manno isomer, the anomerization of the beta-glycoside to the alpha-glycoside as well as the ring contraction of the pyranoside to the furanoside predominated.

  DOI：

  10.1016/s0040-4020(01)89567-3
• 作为产物：
  描述：

  cyclohexyl 4,6-di-O-acetyl-2,3-di-O-benzyl-β-D-mannopyranoside 在 咪唑 、 三乙胺 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 cyclohexyl 2,3-di-O-benzyl-4,6-bis-O-(tert-butyldimethylsilyl)-β-D-mannopyranoside
  参考文献：
  名称：

  Convenient synthesis of pyruvate acetals of carbohydrates by coupling of trialkylsilylated diols and pyruvates

  摘要：

  Hexopyranoside diols, mainly 4,6-diols with alpha-gluco, beta-gluco, alpha-galacto, beta-galacto, and alpha-manno configurations could be converted effectively (40 - 74% yields), to the corresponding pyruvate acetals by the coupling of the O-trialkylsilylated, namely, O-TBDMS and/or O-TMS diols, and ethyl pyruvate in the presence of TMSOTf at temperatures between -30 degrees C and +3 degrees C. In the case of the beta-manno isomer, the anomerization of the beta-glycoside to the alpha-glycoside as well as the ring contraction of the pyranoside to the furanoside predominated.

  DOI：

  10.1016/s0040-4020(01)89567-3