Enantiopure purpurosamine C type glycosyl donors an improved access from rac-Acrolein dimer - Biocatalytic resolution

Article abstract of DOI:10.1016/S0040-4039(97)00448-6

An improved synthetic access to a suitably 'protected' purpurosamine C type glycosyl donor (11, analogously ent-11) starting from racemic 3,4-dihydro-2H-pyran-2-carbaldehyde (rac-1, acrolein dimer) implies an 'indirect aziridination protocol' and a biocatalytic resolution step (acetate hydrolysis, ee > 98). The latter's stereochemical course is confirmed by a highly α-selective glycosylation with an acceptor of known absolute configuration.