(S)-tert-butyl 4-((S,Z)-1,4-dihydroxybut-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate | 1350523-90-8

• 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: (S)-tert-butyl 4-((S,Z)-1,4-dihydroxybut-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate
• 英文别名: tert-butyl (4S)-4-[(Z,1S)-1,4-dihydroxybut-2-enyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 1350523-90-8
• 化学式: C₁₄H₂₅NO₅
• 分子量: 287.356
• InChiKey: DGTDOVUIWIYXGJ-TWHAFNCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  79.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl 4-((S,Z)-1,4-dihydroxybut-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate 在 2,4,6-三异丙基苯磺酰氯 作用下， 以 四氢呋喃 、 hexanes 为溶剂， 反应 14.33h， 以84%的产率得到(S)-tert-butyl 4-((S)-2,5-dihydrofuran-2-yl)-2,2-dimethyloxazolidine-3-carboxylate
  参考文献：
  名称：

  Enantioselective synthesis of Boc-protected norfuranomycins

  摘要：

  Garner's aldehyde is a suitable precursor for the synthesis of both isomers of Boc-protected epi-norfuranomycin. We demonstrate the utility of trisyl chloride as an effective leaving group in the dihydrofuran formation step. We also show that TEMPO/BAIB is an effective oxidant for a-amino alcohols avoiding epimerization of the labile a-proton of the product aldehyde. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.007
• 作为产物：
  描述：

  (S)-4-[(Z)-(S)-4-(tert-butyldimethylsilanyloxy)-1-hydroxybut-2-enyl]-2',2'-dimethyloxazolidine-3'-carboxylic acid tert-butyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以92%的产率得到(S)-tert-butyl 4-((S,Z)-1,4-dihydroxybut-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate
  参考文献：
  名称：

  Enantioselective synthesis of Boc-protected norfuranomycins

  摘要：

  Garner's aldehyde is a suitable precursor for the synthesis of both isomers of Boc-protected epi-norfuranomycin. We demonstrate the utility of trisyl chloride as an effective leaving group in the dihydrofuran formation step. We also show that TEMPO/BAIB is an effective oxidant for a-amino alcohols avoiding epimerization of the labile a-proton of the product aldehyde. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.007

文献信息

• Enantioselective synthesis of Boc-protected norfuranomycins
  作者：Mikko Passiniemi、Ari M.P. Koskinen

  DOI：10.1016/j.tetlet.2011.10.007

  日期：2011.12

  Garner's aldehyde is a suitable precursor for the synthesis of both isomers of Boc-protected epi-norfuranomycin. We demonstrate the utility of trisyl chloride as an effective leaving group in the dihydrofuran formation step. We also show that TEMPO/BAIB is an effective oxidant for a-amino alcohols avoiding epimerization of the labile a-proton of the product aldehyde. (C) 2011 Elsevier Ltd. All rights reserved.