methyl (2S)-2-[(4R,5S)-4-(hydroxymethyl)-2-oxo-1,3-oxazolidin-5-yl]-2-(trimethylacetoxy)acetate | 1071571-93-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2S)-2-[(4R,5S)-4-(hydroxymethyl)-2-oxo-1,3-oxazolidin-5-yl]-2-(trimethylacetoxy)acetate
• CAS: 1071571-93-1
• 化学式: C₁₂H₁₉NO₇
• 分子量: 289.285
• InChiKey: SYDKFNFWOAITBM-CSMHCCOUSA-N

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-[(4R,5S)-4-(hydroxymethyl)-2-oxo-1,3-oxazolidin-5-yl]-2-(trimethylacetoxy)acetate 在 chromium(VI) oxide 、 过碘酸 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 (4S,5S)-5-[(1S)-1-(2,2-dimethylpropanoyloxy)-2-methoxy-2-oxoethyl]-2-oxo-1,3-oxazolidine-4-carboxylic acid
  参考文献：
  名称：

  Efficient and stereoselective synthesis of (2S,3S,4S)-3,4-dihydroxyglutamic acid via intramolecular epoxidation

  摘要：

  The stereoselective synthesis of bioactive (2S,3S,4S)-3,4-dihydroxyglutamic acid hydrochloride salt was achieved. The key step involved an intramolecular nucleophilic epoxidation of homochiral gamma-amino- alpha,beta-unsaturated ester 5 containing an N-hydroperoxymethyl group followed by regioselective opening of the resulting epoxide with neighboring group participation of the N-Boc group. The diastereoselectivity was more than 20:1 by H-1 NMR spectroscopy. Thus, (2S,3S,4S)-3,4-dihydroxyglutamic acid hydrochloride salt was prepared from configurationally stable N-BOC-D-Serinal 4 in 25% overall yield over nine steps. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.07.036
• 作为产物：
  描述：

  methyl 2-{(4R)-4-[(tert-butyldimethylsilyloxy)methyl]-2-oxo-1,3-oxazolidin-5-yl}-2-(trimethylacetoxy)acetate 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以88%的产率得到methyl (2S)-2-[(4R,5S)-4-(hydroxymethyl)-2-oxo-1,3-oxazolidin-5-yl]-2-(trimethylacetoxy)acetate
  参考文献：
  名称：

  Efficient and stereoselective synthesis of (2S,3S,4S)-3,4-dihydroxyglutamic acid via intramolecular epoxidation

  摘要：

  The stereoselective synthesis of bioactive (2S,3S,4S)-3,4-dihydroxyglutamic acid hydrochloride salt was achieved. The key step involved an intramolecular nucleophilic epoxidation of homochiral gamma-amino- alpha,beta-unsaturated ester 5 containing an N-hydroperoxymethyl group followed by regioselective opening of the resulting epoxide with neighboring group participation of the N-Boc group. The diastereoselectivity was more than 20:1 by H-1 NMR spectroscopy. Thus, (2S,3S,4S)-3,4-dihydroxyglutamic acid hydrochloride salt was prepared from configurationally stable N-BOC-D-Serinal 4 in 25% overall yield over nine steps. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.07.036