tert-butyl (R)-4-((R)-hydroxy(2-hydroxy-4,5-dimethoxyphenyl)methyl)-2,2-dimethyloxazolidine-3-carboxylate | 925703-87-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: tert-butyl (R)-4-((R)-hydroxy(2-hydroxy-4,5-dimethoxyphenyl)methyl)-2,2-dimethyloxazolidine-3-carboxylate
• CAS: 925703-87-3
• 化学式: C₁₉H₂₉NO₇
• 分子量: 383.442
• InChiKey: PDVFUUIUCFJCTP-MLGOLLRUSA-N

物化性质

• 沸点：
  529.5±50.0 °C(Predicted)
• 密度：
  1.200±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  97.69
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (R)-4-((R)-hydroxy(2-hydroxy-4,5-dimethoxyphenyl)methyl)-2,2-dimethyloxazolidine-3-carboxylate 在 potassium carbonate 、 对甲苯磺酸 、 sodium iodide 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 18.0h， 生成 tert-butyl (1R,2R)-1-(2-allyloxy-4,5-dimethoxyphenyl)-1,3-dihydroxypropan-2-ylcarbamate
  参考文献：
  名称：

  Synthesis of Protected Chiral Vicinal Diaminoalcohols by Diastereoselective Intramolecular Benzylic Substitution from Bistrichloroacetimidates

  摘要：

  An efficient synthesis of chiral dihydrooxazines (2) from 1-aryl-2-amino-propane-1,3-diols (1) via the corresponding bistrichloroacetimidate intermediates has been developed. In this transformation, one trichloroacetimidate acts as a leaving group and the other acts as a nucleophile. The cyclization proceeds through an S(N)1 mechanism to provide trans-dihydrooxazines with complete diastereoselectivity irrespective of the absolute configuration of the benzylic alcohol. The transformation of 2 into other selectively protected aminodiols is also documented.

  DOI：

  10.1021/ol0627202
• 作为产物：
  描述：

  3,4-二甲氧基苯酚 、 (R)-(+)-3-Boc-2,2-二甲基恶唑啉-4-甲醛 在 甲基氯化镁 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.17h， 以91%的产率得到tert-butyl (R)-4-((R)-hydroxy(2-hydroxy-4,5-dimethoxyphenyl)methyl)-2,2-dimethyloxazolidine-3-carboxylate
  参考文献：
  名称：

  Synthesis of Protected Chiral Vicinal Diaminoalcohols by Diastereoselective Intramolecular Benzylic Substitution from Bistrichloroacetimidates

  摘要：

  An efficient synthesis of chiral dihydrooxazines (2) from 1-aryl-2-amino-propane-1,3-diols (1) via the corresponding bistrichloroacetimidate intermediates has been developed. In this transformation, one trichloroacetimidate acts as a leaving group and the other acts as a nucleophile. The cyclization proceeds through an S(N)1 mechanism to provide trans-dihydrooxazines with complete diastereoselectivity irrespective of the absolute configuration of the benzylic alcohol. The transformation of 2 into other selectively protected aminodiols is also documented.

  DOI：

  10.1021/ol0627202