cyclohexyl 2,3-di-O-benzyl-β-D-glucopyranoside | 160204-40-0

• 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-β-D-glucopyranoside
• CAS: 160204-40-0
• 化学式: C₂₆H₃₄O₆
• 分子量: 442.552
• InChiKey: WXIYMRXLEVZLRW-WSGIOKLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  32.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  77.38
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  cyclohexyl 2,3-di-O-benzyl-β-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 cyclohexyl 2,3-di-O-benzyl-5,6-O-<(1-ethoxycarbonyl)ethylidene>-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：

  1,4,6-三-O-乙酰基-2,3-二-O-苄基-alpha-D-吡喃葡萄糖 在 silver silicate 、 氢溴酸 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 、 甲苯 为溶剂， 反应 0.5h， 生成 cyclohexyl 2,3-di-O-benzyl-β-D-glucopyranoside
  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