methyl (2S)-2-{(4R,5S)-4-[(tert-butyldimethylsilyloxy)methyl]-2-oxo-1,3-oxazolidin-5-yl}-2-hydroxyacetate | 1071571-91-9

• 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-[(tert-butyldimethylsilyloxy)methyl]-2-oxo-1,3-oxazolidin-5-yl}-2-hydroxyacetate
• 英文别名: methyl (2S)-2-[(4R,5S)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-oxo-1,3-oxazolidin-5-yl]-2-hydroxyacetate
• CAS: 1071571-91-9
• 化学式: C₁₃H₂₅NO₆Si
• 分子量: 319.43
• InChiKey: JNHANFOLGWWMPZ-UTLUCORTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.02
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  94.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-[1-(tert-butoxycarbonyl-hydroxymethyl-amino)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-oxirane-2-carboxylic acid methyl ester 以 甲醇 为溶剂， 反应 24.0h， 生成 methyl (2S)-2-{(4R,5S)-4-[(tert-butyldimethylsilyloxy)methyl]-2-oxo-1,3-oxazolidin-5-yl}-2-hydroxyacetate
  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