1979 Volume 27 Issue 11 Pages 2661-2674
All isomeric 1α-, 1β-, 2-, 3-, 4-, and 6-mono-O-acyl-D-glucopyranoses (acyl group from caprinoyl through stearoyl) were synthesized in a regio-(and stereo-) selective manner. Gas-liquid chromatography (trimethylsilyl (TMS) derivatives), infrared, and 1H-nuclear magnetic resonance data, which provided evidence for assignment of the position of the acyl chain, are described. Compounds previously reported to be 2-O-acyl and 3-O-acyl-D-glucoses were shown to be 6-O-acyl derivatives. In the 3-and 6-O-acyl derivatives, anomerization was slow and they were present largely as α-anomers, while the 2-and 4-O-acyl derivatives were mixtures of α-and β-anomers due to their rapid anomerization. Some di-O-acyl-D-glucopyranoses (1β, 6-, 2, 3-, and 4, 6-) and a new tri-O-acyl-D-glucopyranose (2, 4, 6-) were also prepared, all of them except for the 1β, 6-di-O-acyl derivative were obtained as α-anomers.
