(1S,2S,3S,4R,5R)-2-Benzenesulfonyl-3-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-7-oxa-bicyclo[2.2.1]heptane | 139277-10-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2S,3S,4R,5R)-2-Benzenesulfonyl-3-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-7-oxa-bicyclo[2.2.1]heptane
• 英文别名: [(1R,2S,3S,4S,6R)-3-(benzenesulfonyl)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-7-oxabicyclo[2.2.1]heptan-2-yl]oxy-tert-butyl-dimethylsilane
• CAS: 139277-10-4
• 化学式: C₂₅H₄₄O₅SSi₂
• 分子量: 512.858
• InChiKey: XXJNQBFPMMXSSJ-GMISPTPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.03
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,2S,3S,4R,5R)-2-Benzenesulfonyl-3-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-7-oxa-bicyclo[2.2.1]heptane 在 正丁基锂 、 四甲基乙二胺 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以80%的产率得到(1S,2R,6S)-3-Benzenesulfonyl-2-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohex-3-enol
  参考文献：
  名称：

  Strain-directed bridge cleavage of (phenylsulfonyl)-7-oxabicyclo[2.2.1]heptane derivatives: application to the total synthesis of carba-.alpha.-DL-glucopyranose

  摘要：

  New methodology to prepare highly oxygenated cyclohexenylsulfones by regioselective beta-elimination of (phenylsulfonyl)-7-oxabicyclo[2.2.1]heptane derivatives has been developed, and its application to the total synthesis of carba-alpha-DL-glucopyranose is described.

  DOI：

  10.1021/jo00033a002
• 作为产物：
  描述：

  7-oxabicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid 在 咪唑 、 lithium aluminium tetrahydride 、 magnesium monoperoxyphthalate hexahydrate 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 97.0h， 生成 (1S,2S,3S,4R,5R)-2-Benzenesulfonyl-3-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-7-oxa-bicyclo[2.2.1]heptane
  参考文献：
  名称：

  Strain-directed bridge cleavage of (phenylsulfonyl)-7-oxabicyclo[2.2.1]heptane derivatives: application to the total synthesis of carba-.alpha.-DL-glucopyranose

  摘要：

  New methodology to prepare highly oxygenated cyclohexenylsulfones by regioselective beta-elimination of (phenylsulfonyl)-7-oxabicyclo[2.2.1]heptane derivatives has been developed, and its application to the total synthesis of carba-alpha-DL-glucopyranose is described.

  DOI：

  10.1021/jo00033a002

文献信息

• Strain-directed bridge cleavage of (phenylsulfonyl)-7-oxabicyclo[2.2.1]heptane derivatives: application to the total synthesis of carba-.alpha.-DL-glucopyranose
  作者：Jose Luis Acena、Odon Arjona、Roberto Fernandez de la Pradilla、Joaquin Plumet、Alma Viso

  DOI：10.1021/jo00033a002

  日期：1992.3

  New methodology to prepare highly oxygenated cyclohexenylsulfones by regioselective beta-elimination of (phenylsulfonyl)-7-oxabicyclo[2.2.1]heptane derivatives has been developed, and its application to the total synthesis of carba-alpha-DL-glucopyranose is described.