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Mild and General Protocol for Selective Deacetylation of Acetyl/Benzoyl-Protected Carbohydrates Full article

Journal Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263
Output data Year: 2024, Volume: 89, Number: 14, Pages: 10021-10026 Pages count : 6 DOI: 10.1021/acs.joc.4c00900
Authors Abramov Alexander A. 1 , Zinin Alexander I. 2 , Kolotyrkina Natalya G. 2 , Kononov Leonid O. 2 , Shatskiy Andrey 3 , Kärkäs Markus D. 3 , Stepanova Elena V. 3,1
Affiliations
1 Tomsk Polytechnic University, Lenin Avenue 30, 634050 Tomsk, Russia
2 Laboratory of Glycochemistry, N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky prosp. 47, 119991 Moscow, Russia
3 Department of Chemistry, KTH Royal Institute of Technology, SE-100 44 Stockholm, Sweden

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.
Cite: Abramov A.A. , Zinin A.I. , Kolotyrkina N.G. , Kononov L.O. , Shatskiy A. , Kärkäs M.D. , Stepanova E.V.
Mild and General Protocol for Selective Deacetylation of Acetyl/Benzoyl-Protected Carbohydrates
Journal of Organic Chemistry. 2024. V.89. N14. P.10021-10026. DOI: 10.1021/acs.joc.4c00900 WOS Scopus OpenAlex
Identifiers:
Web of science: WOS:001263159200001
Scopus: 2-s2.0-85197638235
OpenAlex: W4400224430
Citing:
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OpenAlex 3
Scopus 2
Web of science 2
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