Simple synthesis of phenylpropenoid β-d-glucopyranoside congeners based on Mizoroki–Heck type reaction of organoboron reagents

Palladium(II)-catalyzed carbon–carbon bond formation between allyl 2,3,4,6-tetra-O-acetyl-β-d-glucopyranoside (3) and phenylboronic acid congeners gave the phenylpropenoid 2,3,4,6-tetra-O-acetyl-β-d-glucopyranoside (4a–f) in good yield. Among them, compounds 4a–c were converted to the naturally occurring phenylpropenoid β-d-glucopyranoside analogues (1a–c).