✦ LIBER ✦

Synthesis of N-β-d-glucopyranosyl derivatives of barbital, phenobarbital, metharbital, and mephobarbital

✍ Scribed by William H. Soine; Phyllis J. Soine; Terry M. England; Bruce W. Overton; Shiva Merat

Publisher: Elsevier Science
Year: 1989
Tongue: English
Weight: 680 KB
Volume: 193
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(89)85110-9

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✦ Synopsis

The condensation of per(trimethyl)silylbarbital and -phenobarbital with 1,2,3,4,6-penta-O-acetyl-beta-D-glucopyranose in the presence of stannic chloride in dichloroethane gave moderate yields of the beta-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 1.c.-m.s. proved to be the most useful methods for characterizing the barbiturate glucosides.

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