Semisynthetic aminoglycoside antibacterials. Part 8. Synthesis of novel pentopyranosyl and pentofuranosyl derivatives of gentamine C1 and C1a

Abstract

The syntheses of a variety of 6-O- and 5-O-pentopyranosyl and -pentofuranosyl derivatives from 1,3,2′,6′-tetrakis-N-benzyloxycarbonylgentamine C_1a and C₁ are described. These include neutral glycosides as well as 3-amino-3-deoxy- and 3-deoxy-3-methylamino-glycosides. The solution conformations of these novel semisynthetic aminoglycoside antibacterials are described.