A ROUTE TO LONG-CHAIN AMINO SUGARS BY THREE SUBSTITUTED THIAZOLES AS AUXILIARIES: THIAZOLE-2-CARBONITRILE N-OXIDE, 2-TRIMETHYLSILYLTHIAZOLE, AND 2-THIAZOLYLMETHYLENETRIPHENYLPHOSPHORANE

Article abstract of DOI:10.1016/S0040-4020(01)85954-8

The nitrile oxide-furan cycloadduct thiazole furoisoxazoline 4a is transformed into the 5-amino-5-deoxy dialdoidofuranose derivative 8 through selective elaboration of the three heterocyclic rings: i) bis-hydroxyalkylation of dihydrofuran carbon-carbon do