3,5-O-benzylidene-α-D-xylofurano<1,2,d>oxazolidin-2'-one | 162553-81-3

• 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: 3,5-O-benzylidene-α-D-xylofurano<1,2,d>oxazolidin-2'-one
• 英文别名: (1S,2R,6S,8R,11S)-11-phenyl-3,7,10,12-tetraoxa-5-azatricyclo[6.4.0.02,6]dodecan-4-one
• CAS: 162553-81-3
• 化学式: C₁₃H₁₃NO₅
• 分子量: 263.25
• InChiKey: URJJFKGKLCTYMH-LVEVGFFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,5-O-benzylidene-α-D-xylofurano<1,2,d>oxazolidin-2'-one 在 正丁基锂 、 lithium diisopropyl amide 作用下， 反应 5.5h， 生成 (3aS,4aR,7S,8aS,8bR)-7-Phenyl-3-((S)-2-phenyl-pent-4-enoyl)-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：

  D-吡喃木糖 在 氯化铵 、 zinc(II) chloride 作用下， 反应 10.0h， 生成 3,5-O-benzylidene-α-D-xylofurano<1,2,d>oxazolidin-2'-one
  参考文献：
  名称：

  d-Xylose derived oxazolidin-2-ones as chiral auxiliaries in stereoselective aldol reactions

  摘要：

  Chiral N-acylated oxazolidin-2-one derivatives from D-xylose have been shown to undergo diastereoselective aldol reactions via their lithium imide enolates to afford beta-hydroxylated products. Aliphatic substrates and aldehydes were shown to yield 'non-Evans' syn-aldols readily interpreted by assuming chelated chair-like transition states. When substrates and aldehydes bearing aromatic groups are used chelated boat- or twist-boat-like transition states seem to become similarly or even more probable so that anti- or syn-aldols are also formed from cis- or trans-enolates, respectively. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00096-7

文献信息

• Resolution of racemic carboxylic and sulfonic acids via D-xylose derived new cyclic carbamate reagents (oxazolidin-2-ones)
  作者：Peter Köll、Arne Lützen

  DOI：10.1016/0957-4166(94)00347-e

  日期：1995.1

  Two new chiral oxazolidin-2-ones have been easily prepared from D-xylose and studied as chiral derivatizing agents (CDA's) for the resolution of racemic carboxylic and sulfonic acids The resultant diastereomers are readily separated by chromatographic methods and easily hydrloyzed to isolate the resolved materials in high optical purities and to return the CDA's for reuse.
• 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.
• 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 aldol reactions
  作者：Arne Lützen、Peter Köll

  DOI：10.1016/s0957-4166(97)00096-7

  日期：1997.4

  Chiral N-acylated oxazolidin-2-one derivatives from D-xylose have been shown to undergo diastereoselective aldol reactions via their lithium imide enolates to afford beta-hydroxylated products. Aliphatic substrates and aldehydes were shown to yield 'non-Evans' syn-aldols readily interpreted by assuming chelated chair-like transition states. When substrates and aldehydes bearing aromatic groups are used chelated boat- or twist-boat-like transition states seem to become similarly or even more probable so that anti- or syn-aldols are also formed from cis- or trans-enolates, respectively. (C) 1997 Elsevier Science Ltd.