Synthesis and Pyrolysis of 6-O-Acetyl-2, 3, 4-tri-O-Isovaleryl-α-D-Glucopyranose

Methyl-6-O-TBDPS-α-D-glucopyranoside (2) was selectively synthesized from methyl-α-D-glucopyranoside with high yield, and then isovalerylated, followed by deprotection, acetylation of 6-site and α-site methoxyl group to form Compound 6 . 6-O-Acetyl-2, 3, 4-tri-O-isovaleryl-α-D-glucopyranose (1) was obtained from the hydrolysis of Compound 6 in the presence of hydrazine acetate. The target compound and intermediates were characterized by HRMS and 1H NMR spectra. The results showed that:synthetic Compound 1 was the target product; Compound 1 could release 38.7 μg/mg of isovaleric acid to cigarette smoke during smoking.