糖誘導体の合成並びに薬剤学的研究 (第4報)

D-Galactose 6-Fatty Acid Monoester類の合成

抄録

Condensation of D-galactose and acetone, with phosphoric acid, phosphorus pentoxide, and zinc chloride as catalysts, affords 1, 2; 3, 4-diisopropylidene-D-galactose whose further condensation with fatty acid chloride, in the presence of pyridine, gave eight kinds of D-galactose esters of fatty acid, e.g. butyrate, m.p. 75.5°; caproate, b.p₂ 167°; caprylate, b.p₂ 180° caprate, b.p_0.02 177°; laurate, b.p_0.035 186°, myristate, b.p_0.001 205° palmitate, b.p_0.005 229° stearate, b.p_0.003 210°. These isopropylidene compounds were hydrolyzed with acid catalyst and D-galactose monoesters of fatty acid were obtained, butyrate and caproate as syrupy substances; caprylate, m.p. 155° (t.p. 112°), caprate, m.p. 168° (t.p. 114°); laurate, m.p. 180° (t.p. 124°), myristate, m.p. 176° (t.p. 121°), palmitate, m.p. 175° (t.p. 121°), and stearate, m.p. 175° (t.p. 119°) (t.p. transition point). Of these, esters of caprylate to stearate are considered to form liquid crystals.