(R)-4-benzyl-3-((S)-5-oxotetrahydrofuran-3-carbonyl)oxazolidin-2-one | 1094530-88-7

• 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: (R)-4-benzyl-3-((S)-5-oxotetrahydrofuran-3-carbonyl)oxazolidin-2-one
• 英文别名: (4R)-4-benzyl-3-[(3S)-5-oxooxolane-3-carbonyl]-1,3-oxazolidin-2-one
• CAS: 1094530-88-7
• 化学式: C₁₅H₁₅NO₅
• 分子量: 289.288
• InChiKey: QWVRMFYBOWYTCZ-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-4-benzyl-3-((S)-5-oxotetrahydrofuran-3-carbonyl)oxazolidin-2-one 在 lithium hydroxide monohydrate 、 双氧水 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以50%的产率得到(-)-(S)-5-oxotetrahydro-3-furancarboxylic acid
  参考文献：
  名称：

  Stereoselective Formation of a Functionalized Dipeptide Isostere by Zinc Carbenoid-Mediated Chain Extension

  摘要：

  The application of a zinc carbenoid-mediated chain-extension reaction to a functionalized peptide isostere is reported. The cleavage site of human CVM protease was utilized as a target for testing the synthetic methodology. The utility of this chain-extension reaction is demonstrated in the preparation of an amino acid-derived alpha-unsubstituted gamma-keto ester, which is incorporated into a framework that mimics a tetrapeptide. The identification of a suitable protecting group strategy facilitated the application of a tandem reaction for the incorporation of an alpha-side chain, and the use of an oxazolidinone auxiliary provided excellent diastereocontrol in a tandem chain-extension-aldol reaction. Stereoselectivity of the tandem chain-extension-aldol reaction was determined through application of a CAN-mediated oxidative cleavage reaction.

  DOI：

  10.1021/jo801993k
• 作为产物：
  描述：

  benzyl [(2S,5S)-6-((R)-4-benzyl-2-oxooxazolidin-3-yl)-5-(hydroxymethyl)-3,6-dioxohexan-2-yl](4-methoxybenzyl)carbamate 在 ammonium cerium (IV) nitrate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 以75%的产率得到(R)-4-benzyl-3-((S)-5-oxotetrahydrofuran-3-carbonyl)oxazolidin-2-one
  参考文献：
  名称：

  Stereoselective Formation of a Functionalized Dipeptide Isostere by Zinc Carbenoid-Mediated Chain Extension

  摘要：

  The application of a zinc carbenoid-mediated chain-extension reaction to a functionalized peptide isostere is reported. The cleavage site of human CVM protease was utilized as a target for testing the synthetic methodology. The utility of this chain-extension reaction is demonstrated in the preparation of an amino acid-derived alpha-unsubstituted gamma-keto ester, which is incorporated into a framework that mimics a tetrapeptide. The identification of a suitable protecting group strategy facilitated the application of a tandem reaction for the incorporation of an alpha-side chain, and the use of an oxazolidinone auxiliary provided excellent diastereocontrol in a tandem chain-extension-aldol reaction. Stereoselectivity of the tandem chain-extension-aldol reaction was determined through application of a CAN-mediated oxidative cleavage reaction.

  DOI：

  10.1021/jo801993k

文献信息

• Stereoselective Formation of a Functionalized Dipeptide Isostere by Zinc Carbenoid-Mediated Chain Extension
  作者：Weimin Lin、Cory R. Theberge、Timothy J. Henderson、Charles K. Zercher、Jerry Jasinski、Ray. J. Butcher

  DOI：10.1021/jo801993k

  日期：2009.1.16

  The application of a zinc carbenoid-mediated chain-extension reaction to a functionalized peptide isostere is reported. The cleavage site of human CVM protease was utilized as a target for testing the synthetic methodology. The utility of this chain-extension reaction is demonstrated in the preparation of an amino acid-derived alpha-unsubstituted gamma-keto ester, which is incorporated into a framework that mimics a tetrapeptide. The identification of a suitable protecting group strategy facilitated the application of a tandem reaction for the incorporation of an alpha-side chain, and the use of an oxazolidinone auxiliary provided excellent diastereocontrol in a tandem chain-extension-aldol reaction. Stereoselectivity of the tandem chain-extension-aldol reaction was determined through application of a CAN-mediated oxidative cleavage reaction.