(2R,3S,4R,5R)-2-[(4-Methylsulfanyl-phenylamino)-methyl]-tetrahydro-pyran-2,3,4,5-tetraol | 501347-36-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (2R,3S,4R,5R)-2-[(4-Methylsulfanyl-phenylamino)-methyl]-tetrahydro-pyran-2,3,4,5-tetraol
• CAS: 501347-36-0
• 化学式: C₁₃H₁₉NO₅S
• 分子量: 301.364
• InChiKey: JXKROILIHYAFAH-FVCCEPFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.38
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  102.18
• 氢给体数：
  5.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5R)-2-[(4-Methylsulfanyl-phenylamino)-methyl]-tetrahydro-pyran-2,3,4,5-tetraol 在 Oxone 、 乙二胺四乙酸 、 硫酸 、 碳酸氢钠 、 三乙胺 、 原甲酸三甲酯 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 9.0h， 生成 (3'aR,5S,7'S,7'aS)-7'-hydroxy-2',2'-dimethyl-3-(4-methylsulfonylphenyl)spiro[1,3-oxazolidine-5,6'-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran]-2-one
  参考文献：
  名称：

  Asymmetric Epoxidation Catalyzed by N-Aryl-Substituted Oxazolidinone-Containing Ketones:  Further Evidence for Electronic Effects

  摘要：

  [GRAPHICS]Ketones containing N-aryl-substituted oxazolidinones have been prepared and investigated for the epoxidation of cis-beta-methylstyrene, styrene, and 1-phenylcyclohexene. The attractive interaction between the phenyl group of the olefin and the oxazolidinone of the catalyst is enhanced by introducing an electron-withdrawing group onto the N-phenyl group of the catalyst. The information obtained gives a better understanding of the ketone-catalyzed epoxidation. In addition, the easy preparation of some of the ketones makes them good candidates for practical use.

  DOI：

  10.1021/ol020229e
• 作为产物：
  描述：

  D-葡萄糖 、 4-氨基茴香硫醚 在 溶剂黄146 作用下， 以 水 、 乙醇 为溶剂， 反应 24.5h， 以41%的产率得到(2R,3S,4R,5R)-2-[(4-Methylsulfanyl-phenylamino)-methyl]-tetrahydro-pyran-2,3,4,5-tetraol
  参考文献：
  名称：

  Asymmetric Epoxidation Catalyzed by N-Aryl-Substituted Oxazolidinone-Containing Ketones:  Further Evidence for Electronic Effects

  摘要：

  [GRAPHICS]Ketones containing N-aryl-substituted oxazolidinones have been prepared and investigated for the epoxidation of cis-beta-methylstyrene, styrene, and 1-phenylcyclohexene. The attractive interaction between the phenyl group of the olefin and the oxazolidinone of the catalyst is enhanced by introducing an electron-withdrawing group onto the N-phenyl group of the catalyst. The information obtained gives a better understanding of the ketone-catalyzed epoxidation. In addition, the easy preparation of some of the ketones makes them good candidates for practical use.

  DOI：

  10.1021/ol020229e