Scheme 4.
Synthesis of di-O- and tri-O-galloyl-d-glucosides, 3–4 and 5–6, from 16 (in total 4.1%, 4.1%, 2.1% and 1.5% yields of 3, 4, 5 and 6 from 16, respectively).
Reagents and conditions: (a) BnG-Cl, in anhydrous pyridine, 60 °C, 48 h; (b) H2, 10% Pa-C, in THF containing 6.7% of aqueous 95% EtOH, 40 °C, 10 atm, 12 h.