Scheme 2.
Preparation of 14–17 from d-glucose.
Reagents and conditions: (a) MeOH, Ac-Cl, refluxing, 72 h; (b) PhCHO, triethyl orthoformate, p-toluenesulfonic acid monohydrate, THF, 85 °C, 16 h; (c) PhCH2Br, NaH, DMF, at room temperature, 4 h; (d) PhCHO, p-toluenesulfonic acid monohydrate, DMF, 85 °C, 16 h. * The intermediate 17 was obtained as a mixture of α,β-anomers.