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Alexander A Abramov¹, Alexander I Zinin², Natalya G Kolotyrkina²

¹Tomsk Polytechnic University, Lenin Avenue 30, 634050 Tomsk, Russia.

The Journal of Organic Chemistry

|July 2, 2024

Abstract:

Herein, we report a mild and general protocol for chemoselective deacetylation of mixed acetyl- and benzoyl-protected carbohydrates under mild acidic conditions. The protocol allows quick access to partially protected carbohydrates, which serve as versatile synthetic intermediates during the total synthesis of various mono- and oligosaccharide targets. The applicability of the developed protocol was successfully demonstrated on a range of carbohydrate substrates of various configurations and substitution patterns featuring functionalized aliphatic and aromatic aglycones. The protocol has shown excellent compatibility with the widely used O-anomeric protecting groups, prespacer aglycones, and thioglycoside glycosyl donors.

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