Pyranoside‐into‐Furanoside Rearrangement of 4‐Pentenyl Glycosides in the Synthesis of a Tetrasaccharide‐Related to Galactan I of Klebsiella pneumoniae

Pyranoside‐into‐Furanoside Rearrangement of 4‐Pentenyl Glycosides in the Synthesis of a Tetrasaccharide‐Related to Galactan I of Klebsiella pneumoniae Full article

Journal

European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690

Output data

Year: 2017, Volume: 2017, Number: 3, Pages: 710-718 Pages count : 9 DOI: 10.1002/ejoc.201601413

Authors

Verkhnyatskaya Stella A. ¹ , Krylov Vadim B. ¹ , Nifantiev Nikolay E. ¹

Affiliations

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

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.

Verkhnyatskaya S.A. , Krylov V.B. , 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. V.2017. N3. P.710-718. DOI: 10.1002/ejoc.201601413 WOS Scopus OpenAlex

≡ Web of science:	WOS:000393330200039
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