Unusual triflic acid-promoted oligomerization of arabinofuranosides during glycosylation

Unusual triflic acid-promoted oligomerization of arabinofuranosides during glycosylation Full article

Journal

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

Output data

Year: 2024, Volume: 540, Article number : 109141, Pages count : DOI: 10.1016/j.carres.2024.109141

Authors

Abronina Polina I. ¹ , Malysheva Nelly N. ¹ , Zinin Alexander I. ¹ , Novikov Dmitry S. ¹ , Panova Maria V. 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

We discovered an unusual triflic acid-promoted oligomerization of arabinofuranosides during glycosylation of the primary hydroxy group of α-(1 → 5)-linked tetraarabinofuranoside bearing 4-(2-chloroethoxy)phenyl aglycone with α-(1 → 5), β-(1 → 2)-linked tetraarabinofuranoside containing N-phenyltrifluoroacetimidoyl leaving group, which led to octa-, dodeca- and hexadecaarabinofuranosides. The possible mechanism of triflic acid-promoted oligomerization was proposed. The choice of promoter was found to be a critical factor for the discovered oligomerization of arabinofuranosides. The obtained octa-, dodeca- and hexadecaarabinofuranosides may serve as useful blocks in the synthesis of oligosaccharide fragments of polysaccharides of Mycobacterium tuberculosis.

Abronina P.I. , Malysheva N.N. , Zinin A.I. , Novikov D.S. , Panova M.V. , Kononov L.O.
Unusual triflic acid-promoted oligomerization of arabinofuranosides during glycosylation
Carbohydrate Research. 2024. V.540. 109141 . DOI: 10.1016/j.carres.2024.109141 WOS Scopus OpenAlex

Web of science:	WOS:001241618500001
Scopus:	2-s2.0-85192524509
OpenAlex:	W4396664876

DB	Citing
OpenAlex	5
Scopus	5
Web of science	5