cyclohexylmethyl 2,3,4,6-tetrakis-O-(triisopropylsilyl)-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cyclohexylmethyl 2,3,4,6-tetrakis-O-(triisopropylsilyl)-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-2-(cyclohexylmethoxy)-3,5-bis[tri(propan-2-yl)silyloxy]-6-[tri(propan-2-yl)silyloxymethyl]oxan-4-yl]oxy-tri(propan-2-yl)silane
• 化学式: C₄₉H₁₀₄O₆Si₄
• 分子量: 901.703
• InChiKey: UOGKDAQLRVFXFK-OOWGBTMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.18
• 重原子数：
  59
• 可旋转键数：
  24
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  ethyl 1-thio-β-D-glucopyranoside 在 2,6-二甲基吡啶 、 三氟甲烷磺酸甲酯 作用下， 以 甲苯 为溶剂， 反应 11.3h， 生成 cyclohexylmethyl 2,3,4,6-tetrakis-O-(triisopropylsilyl)-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