methyl (2S)-2-{(4R,5S)-4-[(tert-butyldimethylsilyloxy)methyl]-2-oxo-1,3-oxazolidin-5-yl}-2-(trimethylacetoxy)acetate | 1071571-92-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: methyl (2S)-2-{(4R,5S)-4-[(tert-butyldimethylsilyloxy)methyl]-2-oxo-1,3-oxazolidin-5-yl}-2-(trimethylacetoxy)acetate
• 英文别名: [(1S)-1-[(4R,5S)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-oxo-1,3-oxazolidin-5-yl]-2-methoxy-2-oxoethyl] 2,2-dimethylpropanoate
• CAS: 1071571-92-0
• 化学式: C₁₈H₃₃NO₇Si
• 分子量: 403.548
• InChiKey: ICJOBUSOGWLWKP-AGIUHOORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  methyl 2-{(4R)-4-[(tert-butyldimethylsilyloxy)methyl]-2-oxo-1,3-oxazolidin-5-yl}-2-hydroxyacetate 、 三甲基乙酸酐 在 4-二甲氨基吡啶 、 TEA 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 methyl (2S)-2-{(4R,5S)-4-[(tert-butyldimethylsilyloxy)methyl]-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