Recently, naturally occurring linear 1,4-glycans have attracted remarkable attention for their activity in cancer and neurodegenerative disease treatment. Classical chemical synthetic strategies for linear 1,4-oligosaccharides are considerably time-consuming due to orthogonal protection/deprotection, the introduction of leaving groups, and various forms of activation of the glycosylation reaction. Herein, we present a new one-pot microwave-activated reiterative assembly of glycal-derived vinyl epoxides in an uncatalyzed substrate-dependent stereospecific process for the preparation of both beta-1,4-d-Gulo and alpha-1,4-d-Manno oligosaccharides.

One-Pot Stereospecific Synthesis of 1,4-Oligosaccharides by Glycal-Derived Vinyl Epoxides Assembly

Santangelo, Maria Chiara
Primo
;
Iacopini, Dalila;Favero, Lucilla;Di Pietro, Sebastiano
Penultimo
;
Di Bussolo, Valeria
Ultimo
2024-01-01

Abstract

Recently, naturally occurring linear 1,4-glycans have attracted remarkable attention for their activity in cancer and neurodegenerative disease treatment. Classical chemical synthetic strategies for linear 1,4-oligosaccharides are considerably time-consuming due to orthogonal protection/deprotection, the introduction of leaving groups, and various forms of activation of the glycosylation reaction. Herein, we present a new one-pot microwave-activated reiterative assembly of glycal-derived vinyl epoxides in an uncatalyzed substrate-dependent stereospecific process for the preparation of both beta-1,4-d-Gulo and alpha-1,4-d-Manno oligosaccharides.
2024
Santangelo, Maria Chiara; Iacopini, Dalila; Favero, Lucilla; Zecchi, Riccardo; Pieraccini, Giuseppe; Di Pietro, Sebastiano; Di Bussolo, Valeria...espandi
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11568/1275028
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