benzyl [(2S,5S)-6-((R)-4-benzyl-2-oxooxazolidin-3-yl)-5-((tert-butyldiphenylsilyloxy)methyl)-3,6-dioxohexan-2-yl](4-methoxybenzyl)carbamate | 1094530-90-1

• 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-((tert-butyldiphenylsilyloxy)methyl)-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-[[tert-butyl(diphenyl)silyl]oxymethyl]-3,6-dioxohexan-2-yl]-N-[(4-methoxyphenyl)methyl]carbamate
• CAS: 1094530-90-1
• 化学式: C₄₉H₅₄N₂O₈Si
• 分子量: 827.062
• InChiKey: LHFXXNBTWDIEMO-PACUZKMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.96
• 重原子数：
  60
• 可旋转键数：
  19
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  112
• 氢给体数：
  0
• 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-((tert-butyldiphenylsilyloxy)methyl)-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87%的产率得到benzyl (2S,5S)-6-((R)-4-benzyl-2-oxooxazolidin-3-yl)-5-((tertbutyldiphenylsilyloxy)methyl)-3,6-dioxohexan-2-ylcarbamate
  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 、 叔丁基二苯基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以78%的产率得到benzyl [(2S,5S)-6-((R)-4-benzyl-2-oxooxazolidin-3-yl)-5-((tert-butyldiphenylsilyloxy)methyl)-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.