4-Methylphenylhydrazine monohydrochloride → Sophorose

Participants

Reaction Conditions

Reaction Steps

This oligosaccharide (5 μmol), sodium acetate (10 μmol) and p-tolylhydrazine hydrochloride (30 μmol) were dissolved in 0.15 mL water in a small vial (Pierce reacti-vial, 0.2 mL capacity, with Tuf-bond Teflon-silicone cap seals). The vial was sealed under argon and warmed on a heating block to 70° C. for 6 hours; the solution became yellow over time and gave a yellow crystalline precipitate, which increased upon cooling to room temperature overnight. The water-insoluble material was the cleavage product, glucose p-tolylosazone (D-arabino-hexos-2-ulose p-tolylosazone). The water soluble fraction contained 2-O-β-D-glucopyranosyl-D-glucose p-tolylhydrazone, and small amounts of D-glucose and the starting oligosaccharide.

Provenance & Evidence