N-propionyl-3,5-O-isopropylidene-α-D-xylofurano<1,2,d>oxazolidin-2'-one | 176965-47-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-propionyl-3,5-O-isopropylidene-α-D-xylofurano<1,2,d>oxazolidin-2'-one
• 英文别名: 1-N,2-O-carbonyl-3,5-O-isopropylidene-N-propionyl-α-D-xylofuranosylamine；(1S,2R,6S,8R)-11,11-dimethyl-5-propanoyl-3,7,10,12-tetraoxa-5-azatricyclo[6.4.0.02,6]dodecan-4-one
• CAS: 176965-47-2
• 化学式: C₁₂H₁₇NO₆
• 分子量: 271.27
• InChiKey: GXKWNJQULOHIDO-NEPJDUFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  N-propionyl-3,5-O-isopropylidene-α-D-xylofurano<1,2,d>oxazolidin-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,8aS,8bR)-3-((S)-2-Bromo-propionyl)-7,7-dimethyl-hexahydro-[1,3]dioxino[4',5':4,5]furo[2,3-d]oxazol-2-one 、 (3aS,4aR,8aS,8bR)-3-((R)-2-Bromo-propionyl)-7,7-dimethyl-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：

  α-D-xylofurano<1,2,d>oxazolidin-2'-one 在 4-二甲氨基吡啶 、 硫酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 N-propionyl-3,5-O-isopropylidene-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

• 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
• 1-<i>N</i>,2-<i>O</i>-Carbonyl-3,5-<i>O</i>-isopropylidene-1-<i>N</i>-[(2<i>R</i>)-2-methyl-3-oxopentanoyl]-α-<scp>D</scp>-xylofuranosylamine
  作者：J. Kopf、A. Lützen、P. Köll

  DOI：10.1107/s0108270199007210

  日期：1999.9.15

  The title compound, C15H21NO7, was synthesized as part of a study involving the testing of new carbohydrate-derived chiral auxiliaries. Its solid-state conformation and absolute configuration were determined. The R configuration for the chiral centre at C-22, created during the synthesis, was deduced from knowledge of the absolute structure of the D-xylose moiety.
• 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 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.