Regioselective acylation of 6-O-protected octyl β-d-glucopyranosides by DMAP catalysis

Regioselectivity of acylation of 6-O-protected octyl β-d-glucopyranosides was investigated. Treatment of octyl 6-O-methyl-β-d-glucopyranoside with isobutyric anhydride in the presence of DMAP in toluene at −40 °C gave 3-O-isobutyryl derivative in >99% regioselectivity. Similar treatment of octyl 6-O-TBS-β-d-glucopyranoside at −20 °C also gave 3-O-isobutyryl derivative in >99% regioselectivity.