3'-(2"(E)hexenoyl)-3,4,6-tri-O-benzoyl-1,2-dideoxy-α-D-glucopyranosido[1,2:5',4']oxazolidin-2'-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3'-(2"(E)hexenoyl)-3,4,6-tri-O-benzoyl-1,2-dideoxy-α-D-glucopyranosido[1,2:5',4']oxazolidin-2'-one
• 英文别名: [(3aR,5R,6S,7R,7aR)-6,7-dibenzoyloxy-1-[(E)-hex-2-enoyl]-2-oxo-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]oxazol-5-yl]methyl benzoate
• 化学式: C₃₄H₃₁NO₁₀
• 分子量: 613.621
• InChiKey: JLDTXSGZDHSROY-YUEWYCLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  45
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  135
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  氯化二乙基铝 、 3'-(2"(E)hexenoyl)-3,4,6-tri-O-benzoyl-1,2-dideoxy-α-D-glucopyranosido[1,2:5',4']oxazolidin-2'-one 在 N-氯代丁二酰亚胺 作用下， 生成 3'-(3"-ethyl-2"-chlorohexanoyl)-3,4,6-tri-O-benzoyl-1,2-dideoxy-α-D-glucopyranosido[1,2:5',4']oxazolidin-2'-one 、 3'-(3"-ethyl-2"-chlorohexanoyl)-3,4,6-tri-O-benzoyl-1,2-dideoxy-α-D-glucopyranosido[1,2:5',4']oxazolidin-2'-one
  参考文献：
  名称：

  β-Branched α-Halo Carboxylic Acid Derivatives via Stereoselective 1,4 Addition of Dialkylaluminum Chlorides to α,β-Unsaturated N-Acyloxazolidinones

  摘要：

  The stereoselective synthesis of beta-branched alpha-halo carboxylic acids containing two newly formed chiral centers is accomplished by a reaction cascade consisting of the 1,4 addition of dialkylaluminum chlorides to alpha,beta-unsaturated N-acyloxazolidinones and subsequent reaction of the intermediate aluminum enolates with N-halosuccinimide. The most efficient stereocontrol in these tandem processes has been achieved with oxazolidinones derived from glucosamine. Not only aryl substituted but also purely aliphatic beta-branched alpha-halo carboxylic acids can be stereoselectively synthesized by this method. However, the reactions of beta-aryl alpha,beta-unsaturated N-acyloxazolidinones show the highest diastereoselectivity and give one out of four possible diastereomers in high excess.

  DOI：

  10.1021/jo9520957

文献信息

• β-Branched α-Halo Carboxylic Acid Derivatives via Stereoselective 1,4 Addition of Dialkylaluminum Chlorides to α,β-Unsaturated <i>N</i>-Acyloxazolidinones
  作者：Karola Rück-Braun、Armin Stamm、Stefan Engel、Horst Kunz

  DOI：10.1021/jo9520957

  日期：1997.2.1

  The stereoselective synthesis of beta-branched alpha-halo carboxylic acids containing two newly formed chiral centers is accomplished by a reaction cascade consisting of the 1,4 addition of dialkylaluminum chlorides to alpha,beta-unsaturated N-acyloxazolidinones and subsequent reaction of the intermediate aluminum enolates with N-halosuccinimide. The most efficient stereocontrol in these tandem processes has been achieved with oxazolidinones derived from glucosamine. Not only aryl substituted but also purely aliphatic beta-branched alpha-halo carboxylic acids can be stereoselectively synthesized by this method. However, the reactions of beta-aryl alpha,beta-unsaturated N-acyloxazolidinones show the highest diastereoselectivity and give one out of four possible diastereomers in high excess.