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Pyranoside‐into‐Furanoside Rearrangement of 4‐Pentenyl Glycosides in the Synthesis of a Tetrasaccharide‐Related to Galactan I of Klebsiella pneumoniae
Author(s) -
Verkhnyatskaya Stella A.,
Krylov Vadim B.,
Nifantiev Nikolay E.
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601413
Subject(s) - tetrasaccharide , chemistry , galactan , anomer , disaccharide , stereochemistry , glycosylation , protecting group , regioselectivity , organic chemistry , polysaccharide , alkyl , catalysis , biochemistry
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.