(3R,4S,5S,6R)-2-(cyclohexylmethoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol | 197016-48-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4S,5S,6R)-2-(cyclohexylmethoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
• CAS: 197016-48-1
• 化学式: C₁₃H₂₄O₆
• 分子量: 276.33
• InChiKey: CXOBIAQSZOENTL-HENWMNBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.62
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.38
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3R,4S,5S,6R)-2-(cyclohexylmethoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.5h， 生成 cyclohexylmethyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 、 cyclohexylmethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Highly β-Selective O-Glucosidation Due to the Restricted Twist-Boat Conformation

  摘要：

  [GRAPHICS]Ethyl 1-thio-2,3,4,6-tetrakis-O-triisopropylsilyl-beta-D-glucopyranoside, ethyl 6-O-benzyl-1-thio-2,3,4-tris-O-triisopropylsilyl-beta-D-glucopyranoside, and ethyl 6-O-pivaloyl-1-thio-2,3,4-tris-O-triisopropylsilyl-beta-D-glucopyranoside induced highly beta-selective O-glucosidations. Among them, the 6-O-pivaloylated substrate provided the best selectivity up to alpha/beta = 3:97 with cyclohexylmethanol, and the substrate was used for glucosidations with secondary and tertiary alcohols in a highly beta-selective manner. The selectivity would be caused by the twist-boat conformation of the pyranose; this is the first beta-selective O-glucosidation based on conformational control of the pyranose ring.

  DOI：

  10.1021/ol070427b
• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 13.0h， 生成 (3R,4S,5S,6R)-2-(cyclohexylmethoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
  参考文献：
  名称：

  Highly β-Selective O-Glucosidation Due to the Restricted Twist-Boat Conformation

  摘要：

  [GRAPHICS]Ethyl 1-thio-2,3,4,6-tetrakis-O-triisopropylsilyl-beta-D-glucopyranoside, ethyl 6-O-benzyl-1-thio-2,3,4-tris-O-triisopropylsilyl-beta-D-glucopyranoside, and ethyl 6-O-pivaloyl-1-thio-2,3,4-tris-O-triisopropylsilyl-beta-D-glucopyranoside induced highly beta-selective O-glucosidations. Among them, the 6-O-pivaloylated substrate provided the best selectivity up to alpha/beta = 3:97 with cyclohexylmethanol, and the substrate was used for glucosidations with secondary and tertiary alcohols in a highly beta-selective manner. The selectivity would be caused by the twist-boat conformation of the pyranose; this is the first beta-selective O-glucosidation based on conformational control of the pyranose ring.

  DOI：

  10.1021/ol070427b