benzyl [(2S,5S)-6-((R)-4-benzyl-2-oxooxazolidin-3-yl)-5-(hydroxymethyl)-3,6-dioxohexan-2-yl](4-methoxybenzyl)carbamate | 1094530-86-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl [(2S,5S)-6-((R)-4-benzyl-2-oxooxazolidin-3-yl)-5-(hydroxymethyl)-3,6-dioxohexan-2-yl](4-methoxybenzyl)carbamate
• 英文别名: benzyl N-[(2S,5S)-6-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-5-(hydroxymethyl)-3,6-dioxohexan-2-yl]-N-[(4-methoxyphenyl)methyl]carbamate
• CAS: 1094530-86-5
• 化学式: C₃₃H₃₆N₂O₈
• 分子量: 588.657
• InChiKey: IAUJYZSQJRTLIU-MXSCXNJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  43
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  聚合甲醛 、 二碘甲烷 、 benzyl (S)-5-((R)-4-benzyl-2-oxooxazolidin-3-yl)-3,5-dioxopentan-2-yl(4-methoxybenzyl)carbamate 在 diethylzinc 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 1.0h， 以68%的产率得到benzyl [(2S,5S)-6-((R)-4-benzyl-2-oxooxazolidin-3-yl)-5-(hydroxymethyl)-3,6-dioxohexan-2-yl](4-methoxybenzyl)carbamate
  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.