One-pot synthesis of C-glycosylic compounds (C-glycosides) from D-glucal, p-tolylsulfenyl chloride and aromatic/heteroaromatic compounds in the presence of Lewis acids.
In the presence of Zn(CN)(2), benzylated 2-thio-2-S-(p-tolyl)pyranosyl chlorides (2) generated in situ from tri-O-benzyl-D-glucal and p-TolSCl, smoothly react with thiophene, 2-methylthiophene, furan, 2-methylfuran, and N-methylpyrrole to give heteroaryl 2-thio-2-S-(p-tolyl)-C-beta-D-glucopyranosylic compounds (C-glycosides) in good yields. Upon treatment with SnCl(4), the reaction of chlorides 2 with thiophene or 1,4-dimethoxybenzene provides the corresponding benzylated C-beta-D-glucofuranosylic derivatives. Under the same conditions, the use of 2-methylthiophene, furan, 2-methylfuran, or N-methylpyrrole yields (2S,3R,4R,5S)-1,3,4-tribenzyloxy-6,6-diheteroaryl-5-(p-tolylthio)-2-hexanoles. Treatment of 2 and mesitylene with AgBF(4) yielded 1,6-anhydro-3,4-di-O-benzyl-2-thio-2-S-(p-tolyl)-beta-D-glucose.
Koikov
Leonid N
LN
Chemistry Department, University of North Dakota, Grand Forks 58202-9024, USA.
Smoliakova
Irina P
IP
Liu
Hui
H
D001593:Benzyl Compounds; D002125:Calcium Gluconate; D002236:Carbohydrate Conformation; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006841:Hydrocarbons, Aromatic; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular
D001593:Benzyl Compounds; D006027:Glycosides; D006841:Hydrocarbons, Aromatic; D007202:Indicators and Reagents; D002125:Calcium Gluconate