126777-79-5

Upstream product

• 72209-11-1 5-ethyl-5-phenyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,4,6(1H,3H,5H)pyrimidinetrione 
• 604-69-3 β-D-glucose pentaacetate 
• 50-06-6 phenobarbital 
• 186581-53-3 diazomethane 
• 72209-10-0 5-ethyl-1-β-D-glucopyranosyl-5-phenyl-2,4,6-(1H,3H,5H)pyrimidinetrione 

Relevant academic research and scientific papers

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.