SYNTHESIS OF AMINO SUGARS VIA ISOXAZOLINES. DL- AND D-LIVIDOSAMINE (2-AMINO-2,3-DIDEOXY-RIBO-HEXOSE) DERIVATIVES FROM 4-VINYL-1,3-DIOXOLANES AND NITROACETALDEHYDE ACETALS

Article abstract of DOI:10.1016/0040-4020(84)80002-2

1,3-Dipolar cycloaddition of nitrile oxides, generated from nitroethanol and nitroacetaldehyde derivatives 3, 21 and 22, respectively, and of benzonitrile oxide to 4-vinyldioxolanes 1,2 gave ca 4:1 erythro/threo mixtures of corresponding isoxazolines.LAH reduction of erytho isoxazolines proceeded with similar (ca4:1) selectivity to furnish protected ribo-amino-polyols 11, 15, 19, DL- and D-lividosamines 31 and 33, respectively, as main products.The DL-lividosamine derivative 33 was obtained pure by crystallization.In the D-series, the corresponding ribo/arabino mixture D-31/D-32 was transformed to the known α-methyl D-lividosaminide D-37.