3'-<(2"E)-3"-phenylpropenoyl>-3,4,6-tri-O-pivaloyl-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)-3"-phenylpropenoyl>-3,4,6-tri-O-pivaloyl-1,2-dideoxy-α-D-glucopyranosido<1,2:5',4'>oxazolidin-2'-one
• 英文别名: [(3aR,5R,6S,7R,7aR)-6,7-bis(2,2-dimethylpropanoyloxy)-2-oxo-1-[(E)-3-phenylprop-2-enoyl]-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]oxazol-5-yl]methyl 2,2-dimethylpropanoate
• 化学式: C₃₁H₄₁NO₁₀
• 分子量: 587.667
• InChiKey: DKRHWLSUDVOIHG-DLBZOLHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  42
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 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)-3"-phenylpropenoyl>-3,4,6-tri-O-pivaloyl-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 2,2-Dimethyl-propionic acid (3aR,5R,6S,7R,7aR)-1-(2-chloro-3-phenyl-pentanoyl)-6-(2,2-dimethyl-propionyloxy)-5-(2,2-dimethyl-propionyloxymethyl)-2-oxo-hexahydro-pyrano[3,2-d]oxazol-7-yl ester
  参考文献：
  名称：

  Kunz, Horst; Rueck, Karola, Angewandte Chemie, 1993, vol. 105, # 3, p. 355 - 377

  摘要：

  DOI：

文献信息

• Stereoselective Conjugate Addition of Mixed Organoaluminum Reagents to α,β-Unsaturated<i>N</i>-Acyloxazolidinones Derived from Carbohydrates
  作者：Horst Kunz、Stephan Elzner、Steffen Maas、Stefan Engel

  DOI：10.1055/s-2004-831173

  日期：——

  β-branched carboxylic acid derivatives was accomplished by conjugate addition of mixed organoaluminum reagents to chiral α,β-unsaturated N-acyloxazolidinones. Mixed organoaluminum reagentswere generated in situ by transmetalation of Grignard or organolithium compounds with methylaluminum dichloride. Efficient stereocontrol was achieved using different bicyclic glycosamine-derived oxazolidinones, yielding

  β-支化羧酸衍生物的立体选择性合成是通过将混合有机铝试剂与手性 α,β-不饱和 N-酰基恶唑烷酮共轭加成来完成的。混合有机铝试剂通过格氏试剂或有机锂化合物与二氯化甲基铝的金属转移原位生成。使用不同的双环糖胺衍生的恶唑烷酮实现了有效的立体控制，产生交替 (R)- 或 (S)- 配置的 β- 支化羧酸衍生物。
• 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.