The Use of Pyranoside-into-Furanoside Rearrangement and Controlled O(5) → O(6) Benzoyl Migration as the Basis of a Synthetic Strategy To Assemble (1→5)- and (1→6)-Linked Galactofuranosyl Chains

The Use of Pyranoside-into-Furanoside Rearrangement and Controlled O(5) → O(6) Benzoyl Migration as the Basis of a Synthetic Strategy To Assemble (1→5)- and (1→6)-Linked Galactofuranosyl Chains Full article

Journal

Organic Letters
ISSN: 1523-7060 , E-ISSN: 1523-7052

Output data

Year: 2016, Volume: 18, Number: 21, Pages: 5504-5507 Pages count : 4 DOI: 10.1021/acs.orglett.6b02735

Authors

Argunov Dmitry 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, LeninskyProspect 47, 119991 Moscow, Russian Federation 47, 119991 Moscow, Russian Federation

A new pyranoside-into-furanoside (PIF) rearrangement of selectively protected galactopyranosides, followed by controlled O(5) → O(6) benzoate migration, gives either 5-OH or 6-OH products. It has been applied for the synthesis of four oligosaccharides related to the galactomannan from Aspergillus fumigatus. The assembly of target oligosaccharides containing both (1→5) and (1→6) linkages between galactofuranosyl residues was performed by applying terminal mannoside and digalactofuranoside blocks, forming a versatile approach toward fungal and bacterial carbohydrate antigens containing both 5-O- and 6-O-substituted galactofuranoside residues.

Argunov D.A. , Krylov V.B. , Nifantiev N.E.
The Use of Pyranoside-into-Furanoside Rearrangement and Controlled O(5) → O(6) Benzoyl Migration as the Basis of a Synthetic Strategy To Assemble (1→5)- and (1→6)-Linked Galactofuranosyl Chains
Organic Letters. 2016. V.18. N21. P.5504-5507. DOI: 10.1021/acs.orglett.6b02735 WOS Scopus OpenAlex

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