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Mild and General Protocol for Selective Deacetylation of Acetyl/Benzoyl-Protected Carbohydrates
Tomsk Polytechnic University, Lenin Avenue 30, 634050 Tomsk, Russia.
Laboratory of Glycochemistry, N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky prosp. 47, 119991 Moscow, Russia.
Laboratory of Glycochemistry, N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky prosp. 47, 119991 Moscow, Russia.
Laboratory of Glycochemistry, N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky prosp. 47, 119991 Moscow, Russia.ORCID iD: 0000-0003-1858-7738
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2024 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 89, no 14, p. 10021-10026Article in journal (Refereed) Published
Abstract [en]

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.

Place, publisher, year, edition, pages
American Chemical Society (ACS) , 2024. Vol. 89, no 14, p. 10021-10026
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Organic Chemistry
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URN: urn:nbn:se:kth:diva-366448DOI: 10.1021/acs.joc.4c00900ISI: 001263159200001PubMedID: 38955329Scopus ID: 2-s2.0-85197638235OAI: oai:DiVA.org:kth-366448DiVA, id: diva2:1982416
Note

QC 20250708

Available from: 2025-07-08 Created: 2025-07-08 Last updated: 2025-07-08Bibliographically approved

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Shatskiy, AndreyKärkäs, Markus D.Stepanova, Elena V

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Kononov, Leonid O.Shatskiy, AndreyKärkäs, Markus D.Stepanova, Elena V
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