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Synthesis of 6,7-dideoxy-7-isothiocyanatoheptoses: stable fully unprotected monosaccharide isothiocyanates
J M Benito1, C Oriz Mellet, J M García Fernández
1Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, Spain.
Abstract:
Methyl 6,7-dideoxy-7-isothiocyanato-alpha-D-gluco (manno)(galacto)-heptopyranosides have been synthesized in four steps by homologation of the respective methyl hexopyranosides via the corresponding heptopyranosydurononitriles. Neither intra- nor intermolecular thiocarbamate formation was observed, even under rather strenuous acidic or basic conditions. The reducing derivative 6,7-dideoxy-7-isothiocyanato-alpha-D-gluco-heptopyranose was also a stable compound in aqueous solution in the absence of base. Formation of a six-membered intramolecular cyclic thiocarbamate was achieved in DMF solution in the presence of triethylamine. The title compounds are the first examples of stable fully unprotected monosaccharide isothiocyanates.