A highly efficient and facile one pot synthesis of novel 1-glycopyranosyl-4-biaryl butenone derivatives

A facile and efficient methodology, comprised of a domino reaction, a Suzuki-Miyaura coupling reaction followed by an aldol condensation has been developed to synthesize novel 1-glycopyranosyl-4-biaryl butenone derivatives in a one-pot fashion. The reaction of C-glycosides 1-C-(beta-D-glucosyl)propan-2-one, 1-C-(beta-D-mannosyl)propan-2-one, 1-C-(beta-D-galactosyl)propan-2-one, 1-C-(beta-D-lactosyl)propan-2-one with 5-bromothiophene-2-carboxaldehyde or 4-bromobenzaldehyde and different boronic acids in the presence of Pd(II)-catalyst and a base in methanol at room temperature produced various chalcone type biphenyl C-glycosides in 75-85% yields.

Automated summary

A facile and efficient methodology was developed for the synthesis of novel 1-glycopyranosyl-4-biaryl butenone derivatives through a domino reaction, a Suzuki-Miyaura coupling reaction, and an aldol condensation. Various chalcone type biphenyl C-glycosides were obtained in 75-85% yields by reacting C-glycosides with different boronic acids in the presence of a Pd(II)-catalyst and a base in methanol at room temperature.