N-[(2S,3S,6S)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-prop-2-enoxy-3,6-dihydro-2H-pyran-3-yl]-2,2,2-trichloroacetamide | 1207071-23-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: N-[(2S,3S,6S)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-prop-2-enoxy-3,6-dihydro-2H-pyran-3-yl]-2,2,2-trichloroacetamide
• CAS: 1207071-23-5
• 化学式: C₂₇H₃₂Cl₃NO₄Si
• 分子量: 569.0
• InChiKey: TYGYDQOFVDVABG-OYDLWJJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  三氯乙腈 、 (2R,3R,6S)-6-allyloxy-2-[(tert-butyldiphenylsilanyloxy)methyl]-3,6-dihydro-2H-pyran-3-ol 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 potassium carbonate 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 74.0h， 生成 N-[(2S,3S,6S)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-prop-2-enoxy-3,6-dihydro-2H-pyran-3-yl]-2,2,2-trichloroacetamide
  参考文献：
  名称：

  Synthesis and applications of a chiral-oxygenated 3-chloro-3,6-dihydro-2H-pyran obtained under Overman rearrangement conditions

  摘要：

  A chlorinated side product was formed under Overman rearrangement conditions from a trichloroacetimidate along with the expected allylic amide. The chlorinated product derived from a hex-2-enopyranoside was obtained in a totally stereoselective manner, and it can be a useful synthetic intermediate for chlorinated sugars. In order to improve the isolated yields of either the expected Overman rearrangement product or the chlorinated compound, we carried out a thorough study on the experimental conditions. The application of the latter for the synthesis of potential calpain inhibitors is also reported. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.10.136

文献信息

• Synthesis and applications of a chiral-oxygenated 3-chloro-3,6-dihydro-2H-pyran obtained under Overman rearrangement conditions
  作者：Ana Montero、Esperanza Benito、Bernardo Herradón

  DOI：10.1016/j.tetlet.2009.10.136

  日期：2010.1

  A chlorinated side product was formed under Overman rearrangement conditions from a trichloroacetimidate along with the expected allylic amide. The chlorinated product derived from a hex-2-enopyranoside was obtained in a totally stereoselective manner, and it can be a useful synthetic intermediate for chlorinated sugars. In order to improve the isolated yields of either the expected Overman rearrangement product or the chlorinated compound, we carried out a thorough study on the experimental conditions. The application of the latter for the synthesis of potential calpain inhibitors is also reported. (C) 2009 Elsevier Ltd. All rights reserved.