(3aS,4aR,7S,8aS,8bR)-7-Phenyl-3-phenylacetyl-hexahydro-[1,3]dioxino[4',5':4,5]furo[2,3-d]oxazol-2-one | 176965-55-2

• 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: (3aS,4aR,7S,8aS,8bR)-7-Phenyl-3-phenylacetyl-hexahydro-[1,3]dioxino[4',5':4,5]furo[2,3-d]oxazol-2-one
• 英文别名: (1S,2R,6S,8R,11S)-11-phenyl-5-(2-phenylacetyl)-3,7,10,12-tetraoxa-5-azatricyclo[6.4.0.02,6]dodecan-4-one
• CAS: 176965-55-2
• 化学式: C₂₁H₁₉NO₆
• 分子量: 381.385
• InChiKey: UMJXTNKOTYFWLM-XZEJUNMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  溴甲苯 、 (3aS,4aR,7S,8aS,8bR)-7-Phenyl-3-phenylacetyl-hexahydro-[1,3]dioxino[4',5':4,5]furo[2,3-d]oxazol-2-one 在 lithium diisopropyl amide 作用下， 生成 (3aS,4aR,7S,8aS,8bR)-3-((R)-2,3-Diphenyl-propionyl)-7-phenyl-hexahydro-[1,3]dioxino[4',5':4,5]furo[2,3-d]oxazol-2-one 、 (3aS,4aR,7S,8aS,8bR)-3-((S)-2,3-Diphenyl-propionyl)-7-phenyl-hexahydro-[1,3]dioxino[4',5':4,5]furo[2,3-d]oxazol-2-one
  参考文献：
  名称：

  D-xylose derived oxazolidin-2-ones as chiral auxiliaries in stereoselective alkylations

  摘要：

  Chiral N-acylated oxazolidin-2-ones readily available from D-xylose have been demonstrated to undergo highly diastereoselective alkylation reactions via their lithium imide enolates to afford alpha-branched products. These are easily purified and hydrolyzed without difficulty allowing isolation of the desired ramified carboxylic acids in high enantiomeric excesses and to return the auxiliaries for reuse. (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00052-3
• 作为产物：
  描述：

  3,5-O-benzylidene-α-D-xylofurano<1,2,d>oxazolidin-2'-one 、 苯乙酰氯 在 正丁基锂 作用下， 生成 (3aS,4aR,7S,8aS,8bR)-7-Phenyl-3-phenylacetyl-hexahydro-[1,3]dioxino[4',5':4,5]furo[2,3-d]oxazol-2-one
  参考文献：
  名称：

  D-xylose derived oxazolidin-2-ones as chiral auxiliaries in stereoselective alkylations

  摘要：

  Chiral N-acylated oxazolidin-2-ones readily available from D-xylose have been demonstrated to undergo highly diastereoselective alkylation reactions via their lithium imide enolates to afford alpha-branched products. These are easily purified and hydrolyzed without difficulty allowing isolation of the desired ramified carboxylic acids in high enantiomeric excesses and to return the auxiliaries for reuse. (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00052-3

文献信息

• D-xylose derived oxazolidin-2-ones as chiral auxiliaries in stereoselective alkylations
  作者：Peter Köll、Arne Lützen

  DOI：10.1016/0957-4166(96)00052-3

  日期：1996.3

  Chiral N-acylated oxazolidin-2-ones readily available from D-xylose have been demonstrated to undergo highly diastereoselective alkylation reactions via their lithium imide enolates to afford alpha-branched products. These are easily purified and hydrolyzed without difficulty allowing isolation of the desired ramified carboxylic acids in high enantiomeric excesses and to return the auxiliaries for reuse. (C) 1996 Elsevier Science Ltd
• D-xylose derived oxazolidin-2-ones as chiral auxiliaries in stereoselective acylations and halogenations
  作者：Arne Lützen、Peter Köll

  DOI：10.1016/s0957-4166(96)00478-8

  日期：1997.1

  Chiral N-acylated oxazolidin-2-ones readily available from D-xylose have been demonstrated to undergo highly diastereoselective acylation reactions via their lithium imide enolates to afford beta-keto imides. These are easily purified and exhibit surprisingly high stability towards epimerization. The glyco-oxazolidin-2-ones can also be used in diastereoselective halogenation reactions via their boron enolates to get alpha-halogenated products. These and the branched N-acyl compounds can be hydrolyzed allowing isolation of the desired halogenated and ramified carboxylic acids and return of the auxiliaries for reuse. (C) 1997, Elsevier Science Ltd.