Add time:08/27/2019         Source:sciencedirect.com

The condensation of per(trimethyl)silylbarbital and -phenobarbital with 1,2,3,4,6-penta-O-acetyl-β-d-glucopyranose in the presence of stannic chloride in dichloroethane gave moderate yields of the β-coupled barbiturate N-d-glucopyranosyl derivatives. Reaction of metharbital and mephobarbital under the same conditions was unsuccessful. The homologous N-methylglucosides were prepared by reaction of the barbital and phenobarbital N-glucosyl derivatives with diazomethane. The diastereomers of the phenobarbital and mephobarbital derivatives were resolved by use of C-18 reverse-phase h.p.l.c. 1H- and 13C-n.m.r. spectroscopy, and thermospray l.c.-m.s. proved to be the most useful methods for characterizing the barbiturate glucosides.

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