Stereoselective synthesis of a branched α-decaglucan

Autor:	Jian Gao, Yanxin Zhang, Qingpeng Zhao, Shihao Zhou, Han Zhang
Rok vydání:	2020
Předmět:	Steric effects chemistry.chemical_classification Stereochemistry Organic Chemistry Convergent synthesis Glycosidic bond Biochemistry Substrate concentration Catalysis chemistry.chemical_compound chemistry Tetrasaccharide Stereoselectivity Glycosyl Physical and Theoretical Chemistry
Zdroj:	Organic & Biomolecular Chemistry. 18:6549-6557
ISSN:	1477-0539 1477-0520
DOI:	10.1039/d0ob01402h
Popis:	The first and convergent synthesis of a branched Arca subcrenata Lischke α-decaglucan containing all of the α-(1 → 3), α-(1 → 4), and α-(1 → 6) glycosyl linkages was efficiently achieved. The tri- and tetrasaccharide fragments and fully protected decasaccharide were assembled in a one-pot manner with excellent α-stereoselectivity, which was secured by the synergistic α-directing effects of the TolSCl/AgOTf catalysis system and the remote participation effect or steric β-shielding of functionalized groups at the donor 6-O-position. Low substrate concentration was revealed to favor the α-stereochemical outcome of glycosylations between bulkier building blocks. The synthetic approach established here would be very useful for the preparation of more complex α-glucans containing different types of glycosidic linkages and branched architectures.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::e6602ca605b94da09295c8e693f9b612 https://doi.org/10.1039/d0ob01402h Zobrazit plný text záznamu