Synthesis of β-Glycosidically Linked Deoxydisaccharides in theL-Ribo Series

Abstract

By Fischer glycosylation, alkylidenation, methylation, and subsequent reaction with dibromomethyl methyl ether L-rhamnose 2 was converted into the L-gluco-configurated glycosyl bromide 5. According to classical routes 2 was transformed into the 2,6-dideoxy compound 7 and further into the acceptor derivative 9 with arabino-configuration. Glycosylation with 5 gave predominantly the β-1 4-linked disaccharides 11. After deacylation and simultaneous Mitsunobu inversion at C-3 and C-3′ the D–B disaccharide unit of kijanimicin was obtained.