Synthesis of hexaarabinofuranoside bearing the 4-(3-azidopropoxy)phenyl aglycone related to the terminal fragment of polysaccharides of mycobacteria

Synthesis of hexaarabinofuranoside bearing the 4-(3-azidopropoxy)phenyl 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: 2024, Volume: 73, Number: 5, Pages: 1417-1425 Pages count : 9 DOI: 10.1007/s11172-024-4260-4

Authors

Abronina P.I. ¹ , Malysheva N.N. ¹ , Zinin A.I. ¹ , Kolotyrkina N.G. ¹ , Kononov L.O. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

A convergent synthesis α-(1→3)-, α-(1→5), β-(1→2)-linked hexaarabinofuranoside related to the terminal fragment of lipoarabinomannan (LAM) and arabinogalactan of mycobacteria as a glycoside with 4-(3-azidopropoxy)phenyl aglycone was accomplished. 4-(3-Azidopropoxy)phenyl aglycone belongs to the class of Janus aglycones, which can be used as both a temporary protective group for the anomeric position of the carbohydrate and a (pre)spacer for the synthesis of neoglycoconjugates. The key step of the synthesis is the formation of 1,2-trans glycosidic linkage with the use of Ara-β-(1→2)-Ara p-tolylthioarabinofuranoside bearing five triisopropylsilyl groups.

Abronina P.I. , Malysheva N.N. , Zinin A.I. , Kolotyrkina N.G. , Kononov L.O.
Synthesis of hexaarabinofuranoside bearing the 4-(3-azidopropoxy)phenyl aglycone related to the terminal fragment of polysaccharides of mycobacteria
Russian Chemical Bulletin. 2024. V.73. N5. P.1417-1425. DOI: 10.1007/s11172-024-4260-4 Scopus OpenAlex

Scopus:	2-s2.0-85196618127
OpenAlex:	W4399899308

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