(4S,5S,2'R,3'R)-3-(3-hydroxy-2-methyl-3-phenyl-1-oxopropyl)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-oxazolidin-2-one | 471243-65-9

• 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: (4S,5S,2'R,3'R)-3-(3-hydroxy-2-methyl-3-phenyl-1-oxopropyl)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-oxazolidin-2-one
• 英文别名: (4S,5S)-4,5-bis[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-[(2R,3R)-3-hydroxy-2-methyl-3-phenylpropanoyl]-1,3-oxazolidin-2-one
• CAS: 471243-65-9
• 化学式: C₂₃H₃₁NO₈
• 分子量: 449.501
• InChiKey: NITMCTYEMVYEQY-VMLRXSKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (4S,5S,2'R,3'R)-3-(3-hydroxy-2-methyl-3-phenyl-1-oxopropyl)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-oxazolidin-2-one 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 生成 (2RS, 3SR)-3-hydroxy-2-methyl-3-phenylpropanoic acid 、 (2R,3R)-(+)-3-hydroxy-2-methyl-3-phenylpropanoic acid
  参考文献：
  名称：

  DIASTEREOSELECTIVE ALKYLATION AND ALDOL REACTIONS MEDIATED BY THE d-MANNITOL-DERIVED OXAZOLIDIN-2-ONE AS A CHIRAL AUXILIARY

  摘要：

  Chiral N-acylated oxazolidin-2-ones readily available from D-mannitol have been demonstrated to undergo highly diastereoselective alkylation reactions via their lithium imide Z-enolates to afford a-branched products. Evans syn and non-Evans syn aldol products were also selectively obtained using this new auxiliary in high diastereomeric purity by simply changing the stoichiometry of TiCl4 and the nature of the amine base.

  DOI：

  10.1081/scc-120015404
• 作为产物：
  描述：

  (4S,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-oxazolidin-2-one 在 正丁基锂 、 四氯化钛 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 (4S,5S,2'R,3'R)-3-(3-hydroxy-2-methyl-3-phenyl-1-oxopropyl)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  DIASTEREOSELECTIVE ALKYLATION AND ALDOL REACTIONS MEDIATED BY THE d-MANNITOL-DERIVED OXAZOLIDIN-2-ONE AS A CHIRAL AUXILIARY

  摘要：

  Chiral N-acylated oxazolidin-2-ones readily available from D-mannitol have been demonstrated to undergo highly diastereoselective alkylation reactions via their lithium imide Z-enolates to afford a-branched products. Evans syn and non-Evans syn aldol products were also selectively obtained using this new auxiliary in high diastereomeric purity by simply changing the stoichiometry of TiCl4 and the nature of the amine base.

  DOI：

  10.1081/scc-120015404

文献信息

• DIASTEREOSELECTIVE ALKYLATION AND ALDOL REACTIONS MEDIATED BY THE <scp>d</scp>-MANNITOL-DERIVED OXAZOLIDIN-2-ONE AS A CHIRAL AUXILIARY
  作者：Si-Min Kim、Jong-Gab Jun

  DOI：10.1081/scc-120015404

  日期：2002.1.1

  Chiral N-acylated oxazolidin-2-ones readily available from D-mannitol have been demonstrated to undergo highly diastereoselective alkylation reactions via their lithium imide Z-enolates to afford a-branched products. Evans syn and non-Evans syn aldol products were also selectively obtained using this new auxiliary in high diastereomeric purity by simply changing the stoichiometry of TiCl4 and the nature of the amine base.