Stereoselective synthesis of (+)-5-thiosucrose and (+)-5-thioisosucrose

Autor:	Junichi Uenishi, Jinhong Pi, Masakazu Tanaka, Atsushi Ueda, Yui Makura
Jazyk:	angličtina
Rok vydání:	2020
Předmět:	chemistry.chemical_classification Anomer Glycosylation Chemistry Stereochemistry General Chemical Engineering Disaccharide General Chemistry Furanose Acceptor Stereocenter chemistry.chemical_compound Stereoselectivity Glycosyl donor
Zdroj:	RSC Advances. 10(16):9730-9735
ISSN:	2046-2069
Popis:	+)-5-Thiosucrose 1, a novel isosteric sulfur analog of sucrose, was synthesized stereoselectively for the first time via indirect β-d-fructofuranosidation involving selective β-d-psicofuranosidation, followed by stereo-inversion of the secondary hydroxy group at the C-3 position on the furanose ring. Glycosidation of protected 5-Thio-d-glucose with a d-psicofuranosyl donor provided β-d-psicofuranosyl 5-Thio-α-d-glucopyranoside and that with d-fructofuranosyl donor gave α-d-fructofuranosyl 5-Thio-α-d-glucopyranoside. Two anomeric stereocenters of the glycosyl donor and acceptor were controlled correctly to provide a single disaccharide among four possible anomeric isomers in the glycosylation. Conversion of the resulting disaccharides afforded (+)-5-Thiosucrose 1 and (+)-5-Thioisosucrose 2 in excellent yields, respectively. Inhibitory activities of 1 and 2 against α-glucosidase in vitro were also examined. RSC Advances, 10(16), pp.9730-9735; 2020
Databáze:	OpenAIRE
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