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Acid-Catalyzed Transformation of Pyranosides into Furanosides as a Tool for Preparation of Furanoside Synthetic Blocks Full article

Journal Organic Letters
ISSN: 1523-7060 , E-ISSN: 1523-7052
Output data Year: 2024, DOI: 10.1021/acs.orglett.4c02984
Authors Argunov Dmitry A. 1 , Aladysheva Uliana S. 1 , Krylov Vadim B. 1,2 , 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
2 Laboratory of Synthetic Glycovaccines, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russian Federation

Abstract: The importance of natural glycoconjugates containing furanoside residues causes a continued demand for the development of efficient methods for the synthesis of corresponding oligosaccharide derivatives to be used as molecular probes in glycobiological studies. Currently, the chemical synthesis of furanose-containing oligosaccharides often represents a significant challenge because of the lack of short, efficient, and reliable methods for the preparation of selectively substituted furanoside blocks. Herein, we report an easy protocol toward galactofuranose-containing molecules based on the unusual equilibrium between pyranoside and furanoside forms observed for a series of substituted galactosides. The method’s utility is illustrated by the syntheses of furanoside-containing oligosaccharides related to the antigenic polysaccharides of Aspergillus fumigatus and Klebsiella pneumoniae O2ac.
Cite: Argunov D.A. , Aladysheva U.S. , Krylov V.B. , Nifantiev N.E.
Acid-Catalyzed Transformation of Pyranosides into Furanosides as a Tool for Preparation of Furanoside Synthetic Blocks
Organic Letters. 2024. DOI: 10.1021/acs.orglett.4c02984 WOS Scopus OpenAlex
Identifiers:
≡ Web of science: WOS:001313783600001
≡ Scopus: 2-s2.0-85204057454
≡ OpenAlex: W4402504354
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