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.

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

DONDONI, Alessandro;FANTIN, Giancarlo;FOGAGNOLO, Marco;MEDICI, Alessandro;PEDRINI, Paola
1988

Abstract

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.
1988
Dondoni, Alessandro; Fantin, Giancarlo; Fogagnolo, Marco; Medici, Alessandro; Pedrini, Paola
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11392/462460
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