Pyranoside‐into‐Furanoside Rearrangement of 4‐Pentenyl Glycosides in the Synthesis of a Tetrasaccharide‐Related to Galactan I of Klebsiella pneumoniae
Тип публикации: Journal Article
Дата публикации: 2017-01-18
scimago Q2
wos Q2
БС2
SJR: 0.558
CiteScore: 4.3
Impact factor: 2.7
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Краткое описание
An efficient strategy for synthesis of a spacer‐armed tetrasaccharide related to galactan I of Klebsiella pneumoniae is described, which uses newly developed acid‐free conditions for the pyranoside‐into‐furanoside (PIF) rearrangement of a digalactoside bearing a 4‐pentenyl group at the anomeric position. The 4‐pentenyl aglycon was successfully used both as a leaving group in the glycosylation of 3‐(trifluoroacetamido)propanol, and as a temporary anomeric protecting group, allowing conversion into an imidate donor. Regioselective coupling of the disaccharide blocks gave the desired tetrasaccharide sequence required for investigation of the interaction of galactan I with immune‐system proteins.
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Verkhnyatskaya S. A., Krylov V., Nifantiev N. E. Pyranoside‐into‐Furanoside Rearrangement of 4‐Pentenyl Glycosides in the Synthesis of a Tetrasaccharide‐Related to Galactan I of Klebsiella pneumoniae // European Journal of Organic Chemistry. 2017. Vol. 2017. No. 3. pp. 710-718.
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Verkhnyatskaya S. A., Krylov V., Nifantiev N. E. Pyranoside‐into‐Furanoside Rearrangement of 4‐Pentenyl Glycosides in the Synthesis of a Tetrasaccharide‐Related to Galactan I of Klebsiella pneumoniae // European Journal of Organic Chemistry. 2017. Vol. 2017. No. 3. pp. 710-718.
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TY - JOUR
DO - 10.1002/ejoc.201601413
UR - https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.201601413
TI - Pyranoside‐into‐Furanoside Rearrangement of 4‐Pentenyl Glycosides in the Synthesis of a Tetrasaccharide‐Related to Galactan I of Klebsiella pneumoniae
T2 - European Journal of Organic Chemistry
AU - Verkhnyatskaya, Stella A
AU - Krylov, Vadim
AU - Nifantiev, Nikolay E.
PY - 2017
DA - 2017/01/18
PB - Wiley
SP - 710-718
IS - 3
VL - 2017
SN - 1434-193X
SN - 1099-0690
ER -
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@article{2017_Verkhnyatskaya,
author = {Stella A Verkhnyatskaya and Vadim Krylov and Nikolay E. Nifantiev},
title = {Pyranoside‐into‐Furanoside Rearrangement of 4‐Pentenyl Glycosides in the Synthesis of a Tetrasaccharide‐Related to Galactan I of Klebsiella pneumoniae},
journal = {European Journal of Organic Chemistry},
year = {2017},
volume = {2017},
publisher = {Wiley},
month = {jan},
url = {https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.201601413},
number = {3},
pages = {710--718},
doi = {10.1002/ejoc.201601413}
}
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Verkhnyatskaya, Stella A., et al. “Pyranoside‐into‐Furanoside Rearrangement of 4‐Pentenyl Glycosides in the Synthesis of a Tetrasaccharide‐Related to Galactan I of Klebsiella pneumoniae.” European Journal of Organic Chemistry, vol. 2017, no. 3, Jan. 2017, pp. 710-718. https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.201601413.
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