(2R,3R)-3-azido-4-(benzyloxy)-2-(tert-butyldimethylsilyloxy)butan-1-ol | 1380426-12-9

• 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)-3-azido-4-(benzyloxy)-2-(tert-butyldimethylsilyloxy)butan-1-ol
• 英文别名: (2R,3R)-3-azido-2-[tert-butyl(dimethyl)silyl]oxy-4-phenylmethoxybutan-1-ol
• CAS: 1380426-12-9
• 化学式: C₁₇H₂₉N₃O₃Si
• 分子量: 351.521
• InChiKey: YLYSSGZQHLEVPX-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  53
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-azido-4-(benzyloxy)-2-(tert-butyldimethylsilyloxy)butan-1-ol 在 水 、 N,N-二异丙基乙胺 、 三苯基膦 、 lithium chloride 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 乙酸乙酯 、 乙腈 为溶剂， 反应 27.0h， 生成
  参考文献：
  名称：

  A concise synthesis of (+)-deoxoprosophylline via Co(III)(salen)-catalyzed two stereocentered HKR of racemic azido epoxides

  摘要：

  An efficient synthesis of (+)-deoxoprosophylline has been achieved in high optical purity (99% ee) from readily available cis-2-butene-1,4-diol. The strategy employs Co-catalyzed Hydrolytic Kinetic Resolution (HKR) of two stereocentered racemic azido epoxides and diastereoselective intramolecular reductive cyclization as key reactions. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.04.067
• 作为产物：
  描述：

  [(2R,3R)-3-azido-1-[tert-butyl(dimethyl)silyl]oxy-4-phenylmethoxybutan-2-yl]oxy-tert-butyl-dimethylsilane 在 camphor-10-sulfonic acid 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以88%的产率得到(2R,3R)-3-azido-4-(benzyloxy)-2-(tert-butyldimethylsilyloxy)butan-1-ol
  参考文献：
  名称：

  A concise synthesis of (+)-deoxoprosophylline via Co(III)(salen)-catalyzed two stereocentered HKR of racemic azido epoxides

  摘要：

  An efficient synthesis of (+)-deoxoprosophylline has been achieved in high optical purity (99% ee) from readily available cis-2-butene-1,4-diol. The strategy employs Co-catalyzed Hydrolytic Kinetic Resolution (HKR) of two stereocentered racemic azido epoxides and diastereoselective intramolecular reductive cyclization as key reactions. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.04.067

文献信息

• A concise synthesis of (+)-deoxoprosophylline via Co(III)(salen)-catalyzed two stereocentered HKR of racemic azido epoxides
  作者：Dattatray A. Devalankar、Arumugam Sudalai

  DOI：10.1016/j.tetlet.2012.04.067

  日期：2012.6

  An efficient synthesis of (+)-deoxoprosophylline has been achieved in high optical purity (99% ee) from readily available cis-2-butene-1,4-diol. The strategy employs Co-catalyzed Hydrolytic Kinetic Resolution (HKR) of two stereocentered racemic azido epoxides and diastereoselective intramolecular reductive cyclization as key reactions. (C) 2012 Elsevier Ltd. All rights reserved.