tert-butyl (R)-4-((R)-2-(methoxycarbonyl)-1-(3,4-dimethoxyphenyl)ethyl)-2,2-dimethyloxazolidine-3-carboxylate | 927683-12-3

• 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 (R)-4-((R)-2-(methoxycarbonyl)-1-(3,4-dimethoxyphenyl)ethyl)-2,2-dimethyloxazolidine-3-carboxylate
• CAS: 927683-12-3
• 化学式: C₂₂H₃₃NO₇
• 分子量: 423.507
• InChiKey: JCITZXVIKIVKSI-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  83.53
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (R)-4-((R)-2-(methoxycarbonyl)-1-(3,4-dimethoxyphenyl)ethyl)-2,2-dimethyloxazolidine-3-carboxylate 在 乙酰氯 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以85%的产率得到methyl (3R,4R)-4-amino-5-hydroxy-3-(3,4-dimethoxyphenyl)pentanoate hydrochloride
  参考文献：
  名称：

  A solution to the stereochemical problems posed by amaryllidaceae constituents using a highly syn-selective arylcuprate conjugate addition to γ-amino and γ-carbamato-α,β-enoates

  摘要：

  Various substituted arylcuprates undergo stereocontrolled additions to L-serine-derived gamma-amino- and gamma-carbamato-alpha,beta-enoates with high syn-selectivities. The stereochemical outcome of these reactions is fully consistent with the reductive elimination-based model proposed previously. This method is well suited for the preparation of a broad range of biologically active amaryllidaceae constituents and their aromatic analogues. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.11.029
• 作为产物：
  描述：

  4-溴黎芦醚 、 tert-butyl (4R)-4-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 在 magnesium 、 copper(l) iodide 、 三甲基氯硅烷 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以70%的产率得到tert-butyl (R)-4-((R)-2-(methoxycarbonyl)-1-(3,4-dimethoxyphenyl)ethyl)-2,2-dimethyloxazolidine-3-carboxylate
  参考文献：
  名称：

  A solution to the stereochemical problems posed by amaryllidaceae constituents using a highly syn-selective arylcuprate conjugate addition to γ-amino and γ-carbamato-α,β-enoates

  摘要：

  Various substituted arylcuprates undergo stereocontrolled additions to L-serine-derived gamma-amino- and gamma-carbamato-alpha,beta-enoates with high syn-selectivities. The stereochemical outcome of these reactions is fully consistent with the reductive elimination-based model proposed previously. This method is well suited for the preparation of a broad range of biologically active amaryllidaceae constituents and their aromatic analogues. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.11.029