Unusual triflic acid-promoted oligomerization of arabinofuranosides during glycosylation
Publication type: Journal Article
Publication date: 2024-06-01
scimago Q3
wos Q2
SJR: 0.423
CiteScore: 4.0
Impact factor: 2.5
ISSN: 00086215, 1873426X
PubMed ID:
38740000
Abstract
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.
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Abronina P. I. et al. Unusual triflic acid-promoted oligomerization of arabinofuranosides during glycosylation // Carbohydrate Research. 2024. Vol. 540. p. 109141.
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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. Vol. 540. p. 109141.
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TY - JOUR
DO - 10.1016/j.carres.2024.109141
UR - https://linkinghub.elsevier.com/retrieve/pii/S0008621524001204
TI - Unusual triflic acid-promoted oligomerization of arabinofuranosides during glycosylation
T2 - Carbohydrate Research
AU - Abronina, Polina I
AU - Malysheva, Nelly N
AU - Zinin, Alexander I.
AU - Novikov, Dmitry S.
AU - Panova, Maria V.
AU - Kononov, Leonid O.
PY - 2024
DA - 2024/06/01
PB - Elsevier
SP - 109141
VL - 540
PMID - 38740000
SN - 0008-6215
SN - 1873-426X
ER -
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@article{2024_Abronina,
author = {Polina I Abronina and Nelly N Malysheva and Alexander I. Zinin and Dmitry S. Novikov and Maria V. Panova and Leonid O. Kononov},
title = {Unusual triflic acid-promoted oligomerization of arabinofuranosides during glycosylation},
journal = {Carbohydrate Research},
year = {2024},
volume = {540},
publisher = {Elsevier},
month = {jun},
url = {https://linkinghub.elsevier.com/retrieve/pii/S0008621524001204},
pages = {109141},
doi = {10.1016/j.carres.2024.109141}
}