Pd-catalyzed synthesis of hetero 1,2-interlinked C -disaccharides by coupling of iodo glycals with glycals

A facile synthesis of C1-C2 interlinked disaccharides is achieved from readily available -glycals and unsubstituted glycals. Ester-protected donors reacted with ether-protected acceptors under Pd-Ag catalysis to access -disaccharides bearing C-3 vinyl ether, which upon ring opening by Lewis acid fur...

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Veröffentlicht in:	Chemical communications (Cambridge, England) England), 2023-07, Vol.59 (59), p.9090-9093
Hauptverfasser:	Rasool, Bisma, Zargar, Irshad Ahmad, Hussain, Nazar, Mukherjee, Debaraj
Format:	Artikel
Sprache:	eng
Schlagworte:	Chemical synthesis Disaccharides Ketones Lewis acid Palladium Ring opening Vinyl ethers
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creator	Rasool, Bisma Zargar, Irshad Ahmad Hussain, Nazar Mukherjee, Debaraj
description	A facile synthesis of C1-C2 interlinked disaccharides is achieved from readily available -glycals and unsubstituted glycals. Ester-protected donors reacted with ether-protected acceptors under Pd-Ag catalysis to access -disaccharides bearing C-3 vinyl ether, which upon ring opening by Lewis acid furnished pi-extended conjugated orthogonally protected chiral ketones. Benzyl deprotection and reduction of the double bonds resulted in a fully saturated disaccharide stable toward acid hydrolysis.
doi_str_mv	10.1039/d3cc02421k
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source	Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects	Chemical synthesis Disaccharides Ketones Lewis acid Palladium Ring opening Vinyl ethers
title	Pd-catalyzed synthesis of hetero 1,2-interlinked C -disaccharides by coupling of iodo glycals with glycals
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