title: Benzoylated ethyl 1-thioglycosides: direct preparation from per-O-benzoylated sugars.
abstract: D-Glucose, lactose, maltose, and melibiose were benzoylated with Bz(2)O-Et(3)N reagent to give fully benzoylated β products. Under the same conditions, D-mannose produced a mixture where the β-benzoate predominated. Treatment of the foregoing compounds with EtSH at slightly elevated temperature (50-60°C) in the presence of BF(3)·Et(2)O as a promoter gave the corresponding ethyl 1-thio glycosides in high yields. The α-products predominated in all cases in the anomeric mixtures formed. Individual products of all reactions were isolated by chromatography, they were obtained in analytically pure state, and were fully characterized by (1)H and (13)C NMR data and physical constants.
authors: NIDDK, LBC, National Institutes of Health, Bethesda, MD 20892-0815, USA.
authors: Deepak
authors: D
authors: Sail
authors: Pavol
authors: P
authors: Kováč
mesh_terms: D001565:Benzoates / Q000138:chemical synthesis* / Q000737:chemistry; D001880:Boranes / Q000737:chemistry; D004187:Disaccharides / Q000138:chemical synthesis*; D005947:Glucose / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D006031:Glycosylation; D013438:Sulfhydryl Compounds / Q000737:chemistry
chemical_list: D001565:Benzoates; D001880:Boranes; D004187:Disaccharides; D013438:Sulfhydryl Compounds; C101707:boron trifluoride etherate; D005947:Glucose; C007638:ethanethiol