cyclohexyl 4,6-di-O-acetyl-2,3-di-O-benzyl-β-D-mannopyranoside | 160204-39-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cyclohexyl 4,6-di-O-acetyl-2,3-di-O-benzyl-β-D-mannopyranoside
• CAS: 160204-39-7
• 化学式: C₃₀H₃₈O₈
• 分子量: 526.627
• InChiKey: RLDHVCISEOKSPD-IXYVTWBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.73
• 重原子数：
  38.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  cyclohexyl 4,6-di-O-acetyl-2,3-di-O-benzyl-β-D-mannopyranoside 在 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 以87%的产率得到cyclohexyl 2,3-di-O-benzyl-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
• 作为产物：
  描述：

  acetyl 4,6-di-O-acetate-2,3-di-O-benzyl-α-D-mannopyranoside 在 silver silicate 、 氢溴酸 作用下， 以 二氯甲烷 、 溶剂黄146 、 甲苯 为溶剂， 反应 0.5h， 生成 cyclohexyl 4,6-di-O-acetyl-2,3-di-O-benzyl-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