tert-butyl (S)-4-((S,E)-4-(tert-butyldimethylsilyloxy)-1-hydroxybut-2-enyl)-2,2-dimethyloxazolidine-3-carboxylate | 1215207-99-0

• 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: tert-butyl (S)-4-((S,E)-4-(tert-butyldimethylsilyloxy)-1-hydroxybut-2-enyl)-2,2-dimethyloxazolidine-3-carboxylate
• 英文别名: tert-butyl (4S)-4-[(E,1S)-4-[tert-butyl(dimethyl)silyl]oxy-1-hydroxybut-2-enyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 1215207-99-0
• 化学式: C₂₀H₃₉NO₅Si
• 分子量: 401.619
• InChiKey: BYFABFZOBPPXRZ-WFPWZJHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  叔丁基二甲基(2-丙炔氧基)硅烷 、 3-反-溴碳-2,2'-二甲基氧酸酯 在 Schwartz's reagent 、 diethylzinc 、 水 、 Rochelle's salt 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.75h， 以78%的产率得到tert-butyl (S)-4-((S,E)-4-(tert-butyldimethylsilyloxy)-1-hydroxybut-2-enyl)-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

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%.