The Overman rearrangement in carbohydrate chemistry: Stereoselective synthesis of functionalized 3-amino-3,6-dihydro-2H-pyrans and incorporation in peptide derivatives

Tetrahedron Letters

Volumn 46, Issue 3, 2005, Pages 401-405

  Montero, Ana ^a   Mann, Enrique ^a   Herradón, Bernardo ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

Amino sugar; Calpain inhibitor; Enkephalin; Overman rearrangement; Peptidomimetic

Indexed keywords

AZIDE; CALPASTATIN; PEPTIDE DERIVATIVE; PYRAN DERIVATIVE; SUGAR;

ARTICLE; CARBOHYDRATE ANALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; PEPTIDE ANALYSIS; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 11144337733     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.11.109     Document Type: Article

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40. The analytical and spectroscopic data for 11 and 12 are indicated below. To identify the signal assignations (that have been done by a combination of mono- and bi-dimensional NMR experiments), we have numbered the atoms in the following manner: unprimed number refer to the pyrane ring and the dipeptide fragment (including the side chains of the amino acids), starting from the pyranosidic oxygen; the primed number (′) indicate the carbon and hydrogen atoms in the allyloxy fragment; and the double-primed (″) numbers denote atoms in the tyrosine derivative fragment (including the side chain).
41. Other peptide-scaffold hybrids (with other scaffolds than carbohydrate) with sequence similarities to enkephalins are also calpain inhibitors (Montero, A. Ph.D. thesis, Autónoma University, Madrid, July 2004)