(S)-2-((S)-1-azido-2-(benzyloxy)ethyl)oxirane | 1380426-10-7

• 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: (S)-2-((S)-1-azido-2-(benzyloxy)ethyl)oxirane
• 英文别名: (2S)-2-[(1S)-1-azido-2-phenylmethoxyethyl]oxirane
• CAS: 1380426-10-7
• 化学式: C₁₁H₁₃N₃O₂
• 分子量: 219.243
• InChiKey: QYGGYUAEMCPNHP-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  36.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-((S)-1-azido-2-(benzyloxy)ethyl)oxirane 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以98%的产率得到[(2R,3R)-3-azido-1-[tert-butyl(dimethyl)silyl]oxy-4-phenylmethoxybutan-2-yl]oxy-tert-butyl-dimethylsilane
  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)-2-azido-1-(benzyloxy)-3,4-epoxybutane 在 (acetao)(aqua)(S,S)-N,N′-bis(3,5-di-tert-butylsalicylidene-1,2-cyclohexanediamino)-cobalt(III) 作用下， 以 水 为溶剂， 反应 12.0h， 以48%的产率得到(2R,3R)-3-azido-4-(benzyloxy)butane-1,2-diol
  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 enantioselective synthesis of 1,4-dideoxy-1,4-imino-d-arabinitol using Co(III)(salen)-catalyzed hydrolytic kinetic resolution of a two-stereocentered anti-azido epoxide
  作者：Rambabu N. Reddi、Pragati K. Prasad、Rupali G. Kalshetti、Arumugam Sudalai

  DOI：10.1016/j.tetasy.2016.10.013

  日期：2017.1

  A concise enantioselective synthesis of 1,4-dideoxy-1,4-imino-D-arabinitol, (+)-DAB-1, has been described in good overall yield (18.1%) and with high enantiomeric purity (up to 98% ee) starting from a simple raw material, cis-2-butene-1,4-diol. The Co-catalyzed hydrolytic kinetic resolution of a two-stereocentered racemic azido epoxide followed by asymmetric dihydroxylation of the alkene and 'one pot' reductive cyclisation of the azido diol are key reactions in the synthetic sequence. (C) 2016 Elsevier Ltd. All rights reserved.