(1R,2S,4S,5R,6S)-6-Hydroxy-5-phenylsulfanyl-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid | 139277-16-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (1R,2S,4S,5R,6S)-6-Hydroxy-5-phenylsulfanyl-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid
• CAS: 139277-16-0
• 化学式: C₁₃H₁₄O₄S
• 分子量: 266.318
• InChiKey: SXSJWVYXAKBNBF-NGDQXYMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.38
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  66.76
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R,2S,4S,5R,6S)-6-Hydroxy-5-phenylsulfanyl-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid 在 氢氧化钾 、 lithium aluminium tetrahydride 、 正丁基锂 、 四甲基乙二胺 、 magnesium monoperoxyphthalate hexahydrate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 4.25h， 生成 (1S,2R,6S)-3-Benzenesulfonyl-2-benzyloxy-6-benzyloxymethyl-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 、 苯次磺酰氯 以 氯仿 为溶剂， 反应 48.0h， 以82%的产率得到(1R,2S,4S,5R,6S)-6-Hydroxy-5-phenylsulfanyl-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid
  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