Synthesis of a Disaccharide Glycosyl Donor for Use in the Assembly of Oligosaccharides Structurally Related to the Repeating Unit of the Main Chain of Rickettsia typhi O-Polysaccharide

Synthesis of a Disaccharide Glycosyl Donor for Use in the Assembly of Oligosaccharides Structurally Related to the Repeating Unit of the Main Chain of Rickettsia typhi O-Polysaccharide Full article

Journal

Russian Journal of General Chemistry
ISSN: 1070-3632 , E-ISSN: 1608-3350

Output data

Year: 2026, Volume: 96, Number: 4, Article number : 48, Pages count : DOI: 10.1134/s1070363225605022

Authors

Volkov Timur M. ¹ , Yashunsky Dmitry V. ¹ , Nifantiev Nikolay E. ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, 119991, Moscow, Russia

Starting from (2-methyl-5-tert-butylphenyl)-2,3-di-O-benzyl-1-thio-β-d-glucopyranoside and phenyl-2-azido-3,4-di-O-acetyl-2-deoxy-1-seleno-α-l-fucopyranoside the (2-methyl-5-tert-butylphenyl)-4-O-(2-azido-3,4-di-O-acetyl-2-deoxy-α-l-fucopyranosyl)-2,3-di-O-benzyl-1-thio-β-d-glucopyranoside was synthesized, which is planned for the use in the assembly of oligosaccharides structurally related to the repeating unit of the R. typhi O-polysaccharide. During this work, the conditions for selective activation selenoglycoside in the glycosylation reaction were selected. It was also shown that the use of MeOTf as a promoter afford chemoselective activation of selenoglycoside in the presence of thioglycoside.

Volkov T.M. , Yashunsky D.V. , Nifantiev N.E.
Synthesis of a Disaccharide Glycosyl Donor for Use in the Assembly of Oligosaccharides Structurally Related to the Repeating Unit of the Main Chain of Rickettsia typhi O-Polysaccharide
Russian Journal of General Chemistry. 2026. V.96. N4. 48 . DOI: 10.1134/s1070363225605022 WOS Scopus OpenAlex

Submitted:	Aug 11, 2025
Published online:	Mar 3, 2026

≡ Web of science:	WOS:001706087100001
≡ Scopus:	2-s2.0-105031804343
≡ OpenAlex:	W7133356094