tert-butyl (4S)-4-[(E,1S)-4-[tert-butyl(dimethyl)silyl]oxy-1-phenylmethoxybut-2-enyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate | 1215208-01-7

• 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: tert-butyl (4S)-4-[(E,1S)-4-[tert-butyl(dimethyl)silyl]oxy-1-phenylmethoxybut-2-enyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 1215208-01-7
• 化学式: C₂₇H₄₅NO₅Si
• 分子量: 491.744
• InChiKey: QSPNEQICLNNFQN-UOGXHXTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.52
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (4S)-4-[(E,1S)-4-[tert-butyl(dimethyl)silyl]oxy-1-phenylmethoxybut-2-enyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 在 四氧化锇 、 水 、 N-甲基吗啉氧化物 作用下， 以 丙酮 为溶剂， 反应 64.0h， 以1.4 g的产率得到tert-butyl (S)-4-((1R,2S,3R)-1-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-2,3-dihydroxybutyl)-2,2-dimethyloxazolidine-3-carboxylate
  参考文献：
  名称：

  Short and Straightforward Synthesis of (−)-1-Deoxygalactonojirimycin

  摘要：

  The mildness and low basicity of vinylzinc species functioning as a nucleophile in addition to alpha-chiral aldehydes is characterized by lack of epimerization of the vulnerable stereogenic center. This is demonstrated by a highly diastereoselective synthesis of 1-deoxygalactonojirimycin in eight steps from commercial starting materials with overall yield of 35%.

  DOI：

  10.1021/ol100037c
• 作为产物：
  描述：

  tert-butyl (S)-4-((S,E)-4-(tert-butyldimethylsilyloxy)-1-hydroxybut-2-enyl)-2,2-dimethyloxazolidine-3-carboxylate 、 溴甲苯 在 sodium hydride 、 四丁基碘化铵 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 16.08h， 生成 tert-butyl (4S)-4-[(E,1S)-4-[tert-butyl(dimethyl)silyl]oxy-1-phenylmethoxybut-2-enyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  Short and Straightforward Synthesis of (−)-1-Deoxygalactonojirimycin

  摘要：

  The mildness and low basicity of vinylzinc species functioning as a nucleophile in addition to alpha-chiral aldehydes is characterized by lack of epimerization of the vulnerable stereogenic center. This is demonstrated by a highly diastereoselective synthesis of 1-deoxygalactonojirimycin in eight steps from commercial starting materials with overall yield of 35%.

  DOI：

  10.1021/ol100037c

文献信息

• Short and Straightforward Synthesis of (−)-1-Deoxygalactonojirimycin
  作者：Oskari K. Karjalainen、Mikko Passiniemi、Ari M. P. Koskinen

  DOI：10.1021/ol100037c

  日期：2010.3.19

  The mildness and low basicity of vinylzinc species functioning as a nucleophile in addition to alpha-chiral aldehydes is characterized by lack of epimerization of the vulnerable stereogenic center. This is demonstrated by a highly diastereoselective synthesis of 1-deoxygalactonojirimycin in eight steps from commercial starting materials with overall yield of 35%.