Application of Ara-β-(1→2)-Ara diarabinofuranosides with O-TBDPS protective groups in the synthesis of the tetra- and dodecaarabinofuranosides – fragments of mycobacterial polysaccharides

Application of Ara-β-(1→2)-Ara diarabinofuranosides with O-TBDPS protective groups in the synthesis of the tetra- and dodecaarabinofuranosides – fragments of mycobacterial polysaccharides Full article

Journal

Carbohydrate Research
ISSN: 1873-426X , E-ISSN: 0008-6215

Output data

Year: 2025, Volume: 556, Article number : 109622, Pages count : DOI: 10.1016/j.carres.2025.109622

Authors

Abronina Polina I ¹ , Novikov Dmitry S ¹ , Malysheva Nelly N ¹ , Zinin Alexander I ¹ , Kolotyrkina Natalia G ¹ , Kononov Leonid O ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky prosp. 47, 119991, Moscow, Russian Federation. Electronic address: polina-abronina@yandex.ru.

The synthesis of Ara-β-(1 → 2)-Ara glycosyl donor containing TBDPS groups starting from the corresponding glycoside with 4-(3-azidopropoxy)phenyl aglycone was performed in high yield. The obtained glycosyl donor was successfully used in the stereocontrolled synthesis of 4-(2-azidoethoxy)phenyl glycosides of linear β-(1 → 2)-, α-(1 → 5)-tetra- and branched β-(1 → 2)-, α-(1 → 3)-, α-(1 → 5)-linked dodecaarabinofuranosides related to the fragments of mycobacterial polysaccharides. These compounds are valuable for the preparation of conjugates that can be used as antigens in the diagnosis of mycobacterial infections. The synthesis of Ara-β-(1 → 2)-Ara glycosyl donor containing TBDPS groups starting from 4-(2-chloropropoxy)phenyl glycoside was found to be less efficient due to side reactions in course of manipulations with protective groups. Thus, during the treatment with TBAF, 4-(3-chloropropoxy)phenyl aglycone was partially converted to the product of substitution (4-(3-fluoropropoxy)phenyl) and elimination (4-allyloxyphenyl). In the course of silylation (TBDPS-Cl/imidazole), the formation of 4-[3-(imidazole-1-yl)propoxy]phenyl derivative was observed.

Abronina P.I. , Novikov D.S. , Malysheva N.N. , Zinin A.I. , Kolotyrkina N.G. , Kononov L.O.
Application of Ara-β-(1→2)-Ara diarabinofuranosides with O-TBDPS protective groups in the synthesis of the tetra- and dodecaarabinofuranosides – fragments of mycobacterial polysaccharides
Carbohydrate Research. 2025. V.556. 109622 . DOI: 10.1016/j.carres.2025.109622 WOS Scopus OpenAlex

Web of science:	WOS:001612434100001
Scopus:	2-s2.0-105012374374
OpenAlex:	W4412867585

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