Approach to the pseudodisaccharides present in (oxy)apramycin. Synthesis of a 4-O-amino-octodiosyl-2-deoxystreptamine from paromamine

Abstract

The synthesis of an N-protected 2′-amino-2′-deoxy-1′-O-(2-deoxystreptamin-4-yl)-α-D-threo-D-gluco-octo-1′,5′:4′,8′-dipyranose in nine steps from paromamine is described; the key steps are the conversion of paromamine into a protected octuronic acid derivative, followed by its 8′,4′-lactonization upon removal of the O-protecting groups, and partial reduction of the resulting ‘trans-decalone-like’ lactone.