The Stereochemical Outcome of Galactosylations Is Influenced by Both the Position and Electron-Withdrawing Power of Distal Acyl Protecting Groups DOI

Line Juul-Madsen,

Nikolai Cordua,

R Greve

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 8, 2025

The stereodirecting effect of various distal benzoyl esters on the anomeric selectivity in galactopyranosylations was investigated. It found that O-6 galactosyl donors phenyl thioglycoside type had a negligible influence selectivity. Instead, α-selective galactosylations were observed with 4-O-benzoyl, 3,4-di-O-benzoyl, and 4,6-di-O-benzoyl protected donors, highly electron-withdrawing p-nitrobenzoyl (pNO2Bz) protecting group providing most galactosylations. Furthermore, α-selectivity enhanced by replacing thiophenyl aglycon functionality reactive cyclohexyl functionality. These findings enabled successful synthesis biologically relevant α-d-Gal(1→4)Gal linkage. obtained results do not suggest participation as course for selectivities.

Language: Английский

The Stereochemical Outcome of Galactosylations Is Influenced by Both the Position and Electron-Withdrawing Power of Distal Acyl Protecting Groups DOI

Line Juul-Madsen,

Nikolai Cordua,

R Greve

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 8, 2025

The stereodirecting effect of various distal benzoyl esters on the anomeric selectivity in galactopyranosylations was investigated. It found that O-6 galactosyl donors phenyl thioglycoside type had a negligible influence selectivity. Instead, α-selective galactosylations were observed with 4-O-benzoyl, 3,4-di-O-benzoyl, and 4,6-di-O-benzoyl protected donors, highly electron-withdrawing p-nitrobenzoyl (pNO2Bz) protecting group providing most galactosylations. Furthermore, α-selectivity enhanced by replacing thiophenyl aglycon functionality reactive cyclohexyl functionality. These findings enabled successful synthesis biologically relevant α-d-Gal(1→4)Gal linkage. obtained results do not suggest participation as course for selectivities.

Language: Английский

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