(5S,8S)-5,12,12-trimethyl-3,6-dioxo-1,11,11-triphenyl-2,10-dioxa-4-aza-11-silatridecane-8-carboxylic acid | 1094530-94-5

• 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: (5S,8S)-5,12,12-trimethyl-3,6-dioxo-1,11,11-triphenyl-2,10-dioxa-4-aza-11-silatridecane-8-carboxylic acid
• 英文别名: (2S,5S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-oxo-5-(phenylmethoxycarbonylamino)hexanoic acid
• CAS: 1094530-94-5
• 化学式: C₃₁H₃₇NO₆Si
• 分子量: 547.723
• InChiKey: NUEMFFUKRCHRIX-ZCYQVOJMSA-N

物化性质

• 沸点：
  665.4±55.0 °C(predicted)
• 密度：
  1.17±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  39
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (5S,8S)-5,12,12-trimethyl-3,6-dioxo-1,11,11-triphenyl-2,10-dioxa-4-aza-11-silatridecane-8-carboxylic acid 、 L-丙氨酸甲酯盐酸盐 在 碳酸氢钠 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以73%的产率得到(S)-methyl 2-((2S,5S)-5-(benzyloxycarbonylamino)-2-((tertbutyldiphenylsilyloxy)methyl)-4-oxohexanamido)propanoate
  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-((tertbutyldiphenylsilyloxy)methyl)-3,6-dioxohexan-2-ylcarbamate 在 lithium hydroxide monohydrate 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 以70%的产率得到(5S,8S)-5,12,12-trimethyl-3,6-dioxo-1,11,11-triphenyl-2,10-dioxa-4-aza-11-silatridecane-8-carboxylic 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

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.