(3aR,4R,7S,7aS)-7-((tert-butyldimethylsilyl)oxy)-4-(((tert-butyldimethylsilyl)oxy)methyl)-1-methyltetrahydro-1H-pyrano[4,3-d]oxazol-2(6H)-one | 1316852-33-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (3aR,4R,7S,7aS)-7-((tert-butyldimethylsilyl)oxy)-4-(((tert-butyldimethylsilyl)oxy)methyl)-1-methyltetrahydro-1H-pyrano[4,3-d]oxazol-2(6H)-one
• 英文别名: (3aR,4R,7S,7aS)-7-[tert-butyl(dimethyl)silyl]oxy-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-1-methyl-4,6,7,7a-tetrahydro-3aH-pyrano[4,3-d][1,3]oxazol-2-one
• CAS: 1316852-33-1
• 化学式: C₂₀H₄₁NO₅Si₂
• 分子量: 431.72
• InChiKey: FXWPFDLPMHEVPQ-VQHPVUNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aR,4R,7S,7aS)-7-((tert-butyldimethylsilyl)oxy)-4-(((tert-butyldimethylsilyl)oxy)methyl)-1-methyltetrahydro-1H-pyrano[4,3-d]oxazol-2(6H)-one 在 DOWEX 50WX₈-400 ion-exchange resin 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 以518 mg的产率得到(3aR,4R,7S,7aS)-7-((tert-butyldimethylsilyl)oxy)-4-(hydroxymethyl)-1-methyltetrahydro-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-butyldimethylsilyl)oxy)methyl)-3,6-dihydro-2H-pyran-3-yl (perfluorobenzoyl)oxycarbamate 在 咪唑 、 potassium osmate(VI) dihydrate 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 5.0h， 生成 (3aR,4R,7S,7aS)-7-((tert-butyldimethylsilyl)oxy)-4-(((tert-butyldimethylsilyl)oxy)methyl)-1-methyltetrahydro-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

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.