(6S,9S,12S,15S)-methyl 12-((tert-butyldiphenylsilyloxy)methyl)-6-(2-(dimethylamino)-2-oxoethyl)-2,2,9,15-tetramethyl-4,7,10,13-tetraoxo-3-oxa-5,8,14-triazahexadecan-16-oate | 1094531-02-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (6S,9S,12S,15S)-methyl 12-((tert-butyldiphenylsilyloxy)methyl)-6-(2-(dimethylamino)-2-oxoethyl)-2,2,9,15-tetramethyl-4,7,10,13-tetraoxo-3-oxa-5,8,14-triazahexadecan-16-oate
• 英文别名: methyl (2S)-2-[[(2S,5S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-5-[[(2S)-4-(dimethylamino)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoyl]amino]-4-oxohexanoyl]amino]propanoate
• CAS: 1094531-02-8
• 化学式: C₃₈H₅₆N₄O₉Si
• 分子量: 740.97
• InChiKey: COAAVECAXTVGAJ-YRUYCOJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  52
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  169
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (6S,9S,12S,15S)-methyl 12-((tert-butyldiphenylsilyloxy)methyl)-6-(2-(dimethylamino)-2-oxoethyl)-2,2,9,15-tetramethyl-4,7,10,13-tetraoxo-3-oxa-5,8,14-triazahexadecan-16-oate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以38%的产率得到(2S)-methyl 2-((3S)-5-((S)-1-((S)-2-(tert-butoxycarbonylamino)-4-(dimethylamino)-4-oxobutanamido)ethyl)-5-hydroxytetrahydrofuran-3-carboxamido)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：

  (2S)-Methyl 2-((5S)-2-((tert-butyldiphenylsilyloxy)methyl)-4-oxo-5-(tosyloxyamino)hexanamido)propanoate 、 N2-[(丁氧基)羰基]-N4,N4-二甲基天冬酰胺 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(6S,9S,12S,15S)-methyl 12-((tert-butyldiphenylsilyloxy)methyl)-6-(2-(dimethylamino)-2-oxoethyl)-2,2,9,15-tetramethyl-4,7,10,13-tetraoxo-3-oxa-5,8,14-triazahexadecan-16-oate
  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.