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Synthesis of a tetrasaccharide containing Janus aglycone related to the terminal fragment of polysaccharides of mycobacteria Full article

Journal Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285
Output data Year: 2023, Volume: 72, Number: 4, Pages: 1046-1058 Pages count : 13 DOI: 10.1007/s11172-023-3870-7
Authors Abronina P.I. 1 , Malysheva N.N. 1 , Zinin A.I. 1 , Kononov L.O. 1
Affiliations
1 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation

Abstract: A convergent synthesis of arabinofuranose-based, α-(1→5), β-(1→2)-linked tetrasaccharide related to the terminal fragment of lipoarabinomannan and arabinogalactan of mycobacteria was carried out. The tetrasaccharide was synthesized as a glycoside with 4-(2-azidoethoxy)phenyl aglycone belonging to the class of Janus aglycones, which can serve as both a temporary protective group of the anomeric position of the carbohydrate residue and a (pre)spacer for the synthesis of neoglycoconjugates (NGCs) useful in the development of new diagnostic agents for tuberculosis. The key step is the formation of a 1,2-cis-glycosidic bond.
Cite: Abronina P.I. , Malysheva N.N. , Zinin A.I. , Kononov L.O.
Synthesis of a tetrasaccharide containing Janus aglycone related to the terminal fragment of polysaccharides of mycobacteria
Russian Chemical Bulletin. 2023. V.72. N4. P.1046-1058. DOI: 10.1007/s11172-023-3870-7 WOS Scopus OpenAlex
Identifiers:
Web of science: WOS:000986557800025
Scopus: 2-s2.0-85159228506
OpenAlex: W4376150598
Citing:
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OpenAlex 8
Scopus 8
Web of science 8
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