(2S)-methyl 2-((3S)-5-((S)-1-((S)-2-(tert-butoxycarbonylamino)-4-(dimethylamino)-4-oxobutanamido)ethyl)-5-hydroxytetrahydrofuran-3-carboxamido)propanoate | 1137734-39-4

• 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: (2S)-methyl 2-((3S)-5-((S)-1-((S)-2-(tert-butoxycarbonylamino)-4-(dimethylamino)-4-oxobutanamido)ethyl)-5-hydroxytetrahydrofuran-3-carboxamido)propanoate
• 英文别名: methyl (2S)-2-[[(3S)-5-[(1S)-1-[[(2S)-4-(dimethylamino)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoyl]amino]ethyl]-5-hydroxyoxolane-3-carbonyl]amino]propanoate
• CAS: 1137734-39-4
• 化学式: C₂₂H₃₈N₄O₉
• 分子量: 502.565
• InChiKey: VLOMICXWHAQFQT-NVNSNGKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  173
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  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