Document Report Card

ID: ALA1121766

Journal: J Med Chem

Title: Chemical modification of aminoglycosides. 3. Synthesis of 2"-deoxykanamycins from neamine.

Authors: Reid RJ, Mizsak SA, Reineke LM, Zurenko GE, Stern KF, Magerlein BJ.

Abstract: The preparation of 2"-deoxykanamycin B (12) and 2",3',4'-trideoxykanamycin B (14) from neamine (1) is described. Key intermediates in the synthesis of these 2"-deoxyaminoglycoside antibiotics are 3',4'-bis-O-(p-nitrobenzoyl)-1,2',3,6'-tetrakis-N-(trifluoroacetyl)neamine (6) and 3',4'-dideoxy-1,2',3,6'-tetrakis-N-(trifluoroacetyl)neamine (9). The amino groups of these intermediates are blocked by the trifluoroacetyl group, a blocking group not widely used in aminoglycoside chemistry.

CiteXplore: 7310825

DOI: 10.1021/jm00144a023