(2R,3R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,6-dihydro-2H-pyran-3-yl (perfluorobenzoyl)oxycarbamate | 1316852-31-9

• 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: (2R,3R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,6-dihydro-2H-pyran-3-yl (perfluorobenzoyl)oxycarbamate
• 英文别名: [[(2R,3R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3,6-dihydro-2H-pyran-3-yl]oxycarbonylamino] 2,3,4,5,6-pentafluorobenzoate
• CAS: 1316852-31-9
• 化学式: C₂₀H₂₄F₅NO₆Si
• 分子量: 497.491
• InChiKey: KEVYBJNBYOBXDS-GHMZBOCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,6-dihydro-2H-pyran-3-yl (perfluorobenzoyl)oxycarbamate 在 potassium osmate(VI) dihydrate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 4.5h， 以63%的产率得到(3aR,4R,7S,7aR)-4-(((tert-butyldimethylsilyl)oxy)methyl)-7-hydroxytetrahydro-1H-pyrano[4,3-d]oxazol-2(6H)-one
  参考文献：
  名称：

  Synthesis of the dysiherbaine tetrahydropyran core utilizing improved tethered aminohydroxylation conditions

  摘要：

  A concise stereoselective route to the dysiherbaine tetrahydropyran core was achieved in nine steps and 39% overall yield. Donohoe's improved tethered aminohydroxylation conditions were employed to concurrently install the amino and alcohol groups and construct the tetrahydropyran ring, which features four contiguous cis-stereocenters. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.05.106
• 作为产物：
  描述：

  (2R,3R)-2-[(tert-butyldimethylsilanyloxy)methyl]-3-hydroxy-3,6-dihydro-2H-pyran 在 吡啶 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 26.0h， 生成 (2R,3R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,6-dihydro-2H-pyran-3-yl (perfluorobenzoyl)oxycarbamate
  参考文献：
  名称：

  Synthesis of the dysiherbaine tetrahydropyran core utilizing improved tethered aminohydroxylation conditions

  摘要：

  A concise stereoselective route to the dysiherbaine tetrahydropyran core was achieved in nine steps and 39% overall yield. Donohoe's improved tethered aminohydroxylation conditions were employed to concurrently install the amino and alcohol groups and construct the tetrahydropyran ring, which features four contiguous cis-stereocenters. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.05.106

文献信息

• Synthesis of the dysiherbaine tetrahydropyran core utilizing improved tethered aminohydroxylation conditions
  作者：Christopher L. Carroll、A. Richard Chamberlin

  DOI：10.1016/j.tetlet.2011.05.106

  日期：2011.8

  A concise stereoselective route to the dysiherbaine tetrahydropyran core was achieved in nine steps and 39% overall yield. Donohoe's improved tethered aminohydroxylation conditions were employed to concurrently install the amino and alcohol groups and construct the tetrahydropyran ring, which features four contiguous cis-stereocenters. (C) 2011 Elsevier Ltd. All rights reserved.