cholestanyl 6-O-pivaloyl-2,3,4-tris-O-(triisopropylsilyl)-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: cholestanyl 6-O-pivaloyl-2,3,4-tris-O-(triisopropylsilyl)-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-6-[[(3S,5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-3,4,5-tris[tri(propan-2-yl)silyloxy]oxan-2-yl]methyl 2,2-dimethylpropanoate
• 化学式: C₆₅H₁₂₆O₇Si₃
• 分子量: 1103.97
• InChiKey: LPUXFFPNWFNNPI-XIFAJEAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.49
• 重原子数：
  75
• 可旋转键数：
  26
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  ethyl 1-thio-β-D-glucopyranoside 在 吡啶 、 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 三氟甲烷磺酸甲酯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 43.5h， 生成 cholestanyl 6-O-pivaloyl-2,3,4-tris-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

文献信息

• Highly β-Selective O-Glucosidation Due to the Restricted Twist-Boat Conformation
  作者：Yasunori Okada、Tatsuya Mukae、Kotaro Okajima、Miyoko Taira、Mari Fujita、Hidetoshi Yamada

  DOI：10.1021/ol070427b

  日期：2007.4.1

  [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.