A simple, stereoselective synthesis of ketomethylene dipeptide isosteres

Tetrahedron

Volumn 53, Issue 21, 1997, Pages 7119-7126

  Hoffman, Robert V ^a   Tao, Junhua ^a  

^a NEW MEXICO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PROTEINASE INHIBITOR; PSEUDOPEPTIDE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030992559     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00410-9     Document Type: Article

References (26)

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24. A referee has suggested that the second equivalent of the 2-triflyloxy ester O-alkylates the β-ketoester rather than the Cbz-group. This appears unlikely since without an amino group at C-4 or using an N,N-dibenzylamino protecting group in place of the Cbz-group requires only one equivalent of the triflate. It is the Cbz group which changes the chemistry and thus seems to be alkylated.
25. The priority rules change in the ketomethylene isostere thus the 2R configuration in the isostere chain corresponds to the 2S configuration in an analogous peptide chain.
26. Elemental analysis C, H, N ±0.4% was obtained for this compound.