(4S,5S)-3-(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 | 471243-55-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,5S)-3-(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-propanoyl-1,3-oxazolidin-2-one
• CAS: 471243-55-7
• 化学式: C₁₆H₂₅NO₇
• 分子量: 343.377
• InChiKey: SZHDNLZTUNGCNI-VCDKRKBESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  83.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  苯甲醛 、 (4S,5S)-3-(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 四甲基乙二胺 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以91%的产率得到(4S,5S,2'S,3'S)-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
• 作为产物：
  描述：

  3-amino-3-deoxy-1,2:5,6-di-O-isopropylidene-D-altritol 在 正丁基锂 、 sodium methylate 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， 反应 3.5h， 生成 (4S,5S)-3-(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.