A Route to long-chain amino sugars by three substituted thiazoles as auxiliaries: thiazole-2-carbonitrile N-oxide, 2-trimethylsilylthiazole, and 2-thiazolylmethylenetriphenylphosphorane

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 double bond; ii) reductive cleavage of the isoxazoline ring; iii) conversion of thiazole into formyl. One- and two-carbon chain extension of the resulting amino hexose by reaction with 2-trimethylsilylthiazole and 2-thiazolylmethylenetriphenyl-phosphorane respectively affords C7 and C8 homologues. © 1988.