(4S,5S)-3-benzyl-5-(hydroxymethyl)-4-methyloxazolidin-2-one | 1179529-31-7

• 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: (4S,5S)-3-benzyl-5-(hydroxymethyl)-4-methyloxazolidin-2-one
• 英文别名: (4S,5S)-5-(Hydroxymethyl)-4-methyl-3-(phenylmethyl)-2-oxazolidinone；(4S,5S)-3-benzyl-5-(hydroxymethyl)-4-methyl-1,3-oxazolidin-2-one
• CAS: 1179529-31-7
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: YPHJFSBRKDOOJF-GXSJLCMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (S)-3-(dibenzylamino)-1-[(R)-p-tolylsulfinyl]butan-2-one 在 ammonium cerium (IV) nitrate 、 溴代叔丁烷 、 trimethoxonium tetrafluoroborate 、 zinc(II) iodide 作用下， 以 二氯甲烷 、 氯仿 、 水 、 乙腈 为溶剂， 反应 9.0h， 生成 (4S,5S)-3-benzyl-5-(hydroxymethyl)-4-methyloxazolidin-2-one
  参考文献：
  名称：

  Stereoselective divergent synthesis of 1,2-aminoalcohol-containing heterocycles from a common chiral nonracemic building block

  摘要：

  gamma-N,N-Dibenzylamino-beta-hydroxysulfoxide 1 proved to be an excellent chiral building block for the synthesis of a range of 1,2-amino alcohol-containing heterocycles. Thus, I was converted into 4,5-disubstuted oxazolidin-2-one 4 and aminoepoxides 2 and 3. Aminoepoxide 2 proved to be an excellent precursor to access oxazolidin-2-one 5 and azetidin-3-ol 6. Finally, 2 was used as a key intermediate that allowed the development of a divergent strategy to access cis-2-methyl-6-substituted piperidin-3-ol alkaloids. (+)-Deoxocassine 7 and a C-6 ethyl analogue 8 were prepared to illustrate this approach and to demonstrate that this strategy should be adaptable to the production of other members of this alkaloid family. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.11.008

文献信息

• Enantioselective Synthesis of Oxazolidinones from <i>N</i>,<i>N</i>-Dibenzylamino Epoxides
  作者：J. Palenzuela、Gabriel Vargas、María Afonso

  DOI：10.1055/s-0029-1217161

  日期：——

  Enantiomerically pure oxazolidinones are easily prepared from N,N-dibenzylamino epoxides through a one-pot procedure involving monodeprotection of the amino group and treatment with NaHCO3.

  对映体纯度极高的噁唑烷酮类化合物很容易从 N,N-二苄基氨基环氧化物中制备出来，制备过程只需对氨基进行单保护并用 NaHCO3 进行处理。
• Stereoselective divergent synthesis of 1,2-aminoalcohol-containing heterocycles from a common chiral nonracemic building block
  作者：Pierre-Yves Géant、Erwann Grenet、Jean Martínez、Xavier J. Salom-Roig

  DOI：10.1016/j.tetasy.2015.11.008

  日期：2016.1

  gamma-N,N-Dibenzylamino-beta-hydroxysulfoxide 1 proved to be an excellent chiral building block for the synthesis of a range of 1,2-amino alcohol-containing heterocycles. Thus, I was converted into 4,5-disubstuted oxazolidin-2-one 4 and aminoepoxides 2 and 3. Aminoepoxide 2 proved to be an excellent precursor to access oxazolidin-2-one 5 and azetidin-3-ol 6. Finally, 2 was used as a key intermediate that allowed the development of a divergent strategy to access cis-2-methyl-6-substituted piperidin-3-ol alkaloids. (+)-Deoxocassine 7 and a C-6 ethyl analogue 8 were prepared to illustrate this approach and to demonstrate that this strategy should be adaptable to the production of other members of this alkaloid family. (C) 2015 Elsevier Ltd. All rights reserved.