Synthesis of 6-O-Acetyl-2,3,4-tri-O-isobutyryl-β-D-glucopyranose and its Application in Cigarette

6-O-trityl-β-D-methylglucopyranoside(Ⅱ) was selectively synthesized from β-D-methylglucopyranoside(Ⅰ),and then isobutyrylated,followed by detritylation to obtain 2,3,4-tri-O-isobutyryl-β-D-methylglucopyranoside(Ⅲ),which was subsequently acetylated to obtain 6-O-acetyl-2,3,4-tri-O-isobutyryl-β-D-methylglucopyranoside(Ⅳ).Finally,6-O-acetyl-2,3,4-tri-O-isobutyryl-β-D-glucopyranose(Ⅴ) was prepared from the hydrolysis of Ⅳ at the presence of dry hydrogen bromide in glacial acetic acid.The products of all reaction steps were characterized with IR and ¹HNMR.The cigarette applied with V was panel tested and the isobutyric acid in mainstream cigarette smoke was analyzed by GC/MS.The results showed that:1) the synthesized compound Ⅴ was the target product;2) the isobutyric acid in cigarette smoke increased by 26.10 μg per milligram of Ⅴ added;3) cigarette smoke was milder and more harmonious,had less offensive odor and irritation,and better aftertaste by Ⅴ application.