Mild and General Protocol for Selective Deacetylation of Acetyl/Benzoyl-Protected Carbohydrates.
Alexander A AbramovAlexander I ZininNatalya G KolotyrkinaLeonid O KononovAndrey ShatskiyMarkus D KärkäsElena V StepanovaPublished in: The Journal of organic chemistry (2024)
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.