(3aS,4aR,8aS,8bR)-3-((2S,3R)-2-Benzyl-3-hydroxy-butyryl)-7,7-dimethyl-hexahydro-[1,3]dioxino[4',5':4,5]furo[2,3-d]oxazol-2-one | 191287-33-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,4aR,8aS,8bR)-3-((2S,3R)-2-Benzyl-3-hydroxy-butyryl)-7,7-dimethyl-hexahydro-[1,3]dioxino[4',5':4,5]furo[2,3-d]oxazol-2-one
• 英文别名: (1S,2R,6S,8R)-5-[(2S,3R)-2-benzyl-3-hydroxybutanoyl]-11,11-dimethyl-3,7,10,12-tetraoxa-5-azatricyclo[6.4.0.02,6]dodecan-4-one
• CAS: 191287-33-9
• 化学式: C₂₀H₂₅NO₇
• 分子量: 391.421
• InChiKey: VCVYBQJRBFGLCC-XUURAARJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  94.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3aS,4aR,8aS,8bR)-3-((2S,3R)-2-Benzyl-3-hydroxy-butyryl)-7,7-dimethyl-hexahydro-[1,3]dioxino[4',5':4,5]furo[2,3-d]oxazol-2-one 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 syn-2,3-2-benzyl-3-hydroxy-butanoic acid
  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
• 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 、 lithium hexamethyldisilazane 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 (3aS,4aR,8aS,8bR)-3-((2S,3R)-2-Benzyl-3-hydroxy-butyryl)-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 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 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.