Synthesis of N-beta-D-glucopyranosyl derivatives of barbital, phenobarbital, metharbital, and mephobarbital.
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.
Soine
W H
WH
Department of Medical Chemistry, School of Pharmacy, Virginia Commonwealth University, Richmond 23298-0581.
Soine
P J
PJ
England
T M
TM
Overton
B W
BW
Merat
S
S
D001462:Barbital / Q000031:analogs & derivatives / Q000138:chemical synthesis; D001463:Barbiturates / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D002851:Chromatography, High Pressure Liquid; D004187:Disaccharides / Q000138:chemical synthesis; D009682:Magnetic Resonance Spectroscopy; D008618:Mephobarbital / Q000031:analogs & derivatives / Q000138:chemical synthesis; D010634:Phenobarbital / Q000031:analogs & derivatives / Q000138:chemical synthesis
D001463:Barbiturates; D004187:Disaccharides; D008618:Mephobarbital; D001462:Barbital; C043855:phenobarbital-N-glucoside; D010634:Phenobarbital