methyl (2R,4R)-2-tert-butyl-4-methyl-4-[2-(thiophen-2-yl)ethyl]-1,3-oxazolidine-3-carboxylate | 1312772-38-5

• 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: methyl (2R,4R)-2-tert-butyl-4-methyl-4-[2-(thiophen-2-yl)ethyl]-1,3-oxazolidine-3-carboxylate
• 英文别名: methyl (2R,4R)-2-tert-butyl-4-methyl-4-(2-thiophen-2-ylethyl)-1,3-oxazolidine-3-carboxylate
• CAS: 1312772-38-5
• 化学式: C₁₆H₂₅NO₃S
• 分子量: 311.445
• InChiKey: MQEJXWDKFRBRSX-CZUORRHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  67
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2R,4S)-(-)-Dimethyl-2-(1,1-dimethylethyl)-3,4-oxazolidindicarboxylat 在 sodium hypochlorite 、 钾硼氢 、 2,2,6,6-四甲基哌啶氧化物 、 20% palladium hydroxide on carbon 、 potassium tert-butylate 、 氢气 、 碳酸氢钠 、 sodium bromide 、 lithium chloride 作用下， 以 四氢呋喃 、 tetraethylene glycol dimethyl ether 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 26.75h， 生成 methyl (2R,4R)-2-tert-butyl-4-methyl-4-[2-(thiophen-2-yl)ethyl]-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  Asymmetric synthesis of α,α-disubstituted α-amino alcohol derivatives

  摘要：

  Herein we report the asymmetric synthesis of alpha,alpha-disubstituted alpha-amino alcohol derivatives 22, 25 and 26, key intermediates of a novel immunomodulator, using Seebach's method. This synthetic method can be applied to the large scale synthesis of chiral sphingosine 1-phosphate-1 (S1P(1)) receptor agonists, with significant improvements to the previously reported method with regard to the reaction temperature. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.02.006

文献信息

• Asymmetric synthesis of α,α-disubstituted α-amino alcohol derivatives
  作者：Yukiko Iio、Makoto Yamaoka、Masayoshi Jin、Yoshitaka Nakamura、Takahide Nishi

  DOI：10.1016/j.tetasy.2011.02.006

  日期：2011.2

  Herein we report the asymmetric synthesis of alpha,alpha-disubstituted alpha-amino alcohol derivatives 22, 25 and 26, key intermediates of a novel immunomodulator, using Seebach's method. This synthetic method can be applied to the large scale synthesis of chiral sphingosine 1-phosphate-1 (S1P(1)) receptor agonists, with significant improvements to the previously reported method with regard to the reaction temperature. (C) 2011 Elsevier Ltd. All rights reserved.