糖アルキル誘導体の合成並びに薬剤学的研究 (第3報)

Glucose 3-Fatty Acid Monoesterの合成

抄録

Condensation of D-glucose and acetone in the presence of phosphoric acid, phosphorus pentoxide, and zinc chloride afforded 1, 2; 5, 6-diisopropylidene-D-glucose and its condensation with fatty acid chlorides in the presence of pyridine gave eight kinds of diisopropylidene-D-glucose 3-fatty acid monoesters: Butyrate, b.p₃ 149°; caproate, bp₃ 163°; caprylate, b.p₃ 178°, caprate, b.p_0.01 206°; laurate, b.p_0.03 191°; myristate, b.p_0.02 192°; palmitate, b.p_0.2 235°; and stearate, b.p_0.2 255°. Hydrolysis of these esters with acid catalyst gave D-glucose 3-fatty acid monoesters: Butyrate, syrup; caproate, syrup; caprylate, syrup; caprate, m.p. 161° (t.p. 133°); laurate, m.p. 178° (t.p. 137°); myristate, m.p. 178° (t.p. 137°) palmitate, m.p. 177° (t.p. 136°); and stearate, m.p. 160° (t.p. 133°) (t.p.: Transition point).