(3aS,4aR,7S,8aS,8bR)-7-Phenyl-3-propionyl-hexahydro-[1,3]dioxino[4',5':4,5]furo[2,3-d]oxazol-2-one | 176965-48-3

• 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: (3aS,4aR,7S,8aS,8bR)-7-Phenyl-3-propionyl-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-propanoyl-3,7,10,12-tetraoxa-5-azatricyclo[6.4.0.02,6]dodecan-4-one
• CAS: 176965-48-3
• 化学式: C₁₆H₁₇NO₆
• 分子量: 319.314
• InChiKey: IYYWHGHAFYTKAI-HUGQBSPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (3aS,4aR,7S,8aS,8bR)-7-Phenyl-3-propionyl-hexahydro-[1,3]dioxino[4',5':4,5]furo[2,3-d]oxazol-2-one 在 N-溴代丁二酰亚胺(NBS) 、 三氟甲磺酸二丁硼 、 N,N-二异丙基乙胺 作用下， 生成 (3aS,4aR,7S,8aS,8bR)-3-((S)-2-Bromo-propionyl)-7-phenyl-hexahydro-[1,3]dioxino[4',5':4,5]furo[2,3-d]oxazol-2-one 、 (3aS,4aR,7S,8aS,8bR)-3-((R)-2-Bromo-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 acylations and halogenations

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(96)00478-8
• 作为产物：
  描述：

  丙酰氯 、 3,5-O-benzylidene-α-D-xylofurano<1,2,d>oxazolidin-2'-one 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (3aS,4aR,7S,8aS,8bR)-7-Phenyl-3-propionyl-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 acylations and halogenations

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(96)00478-8

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.