Unexpected formation of furanose form during deacetylation of pyranose glyco-oxazolines

Unexpected formation of furanose form during deacetylation of pyranose glyco-oxazolines Full article

Journal

Carbohydrate Research
ISSN: 1873-426X , E-ISSN: 0008-6215

Output data

Year: 2026, Volume: 559, Article number : 109761, Pages count : DOI: 10.1016/j.carres.2025.109761

Authors

Romanyuk Maxim A. ¹ , Myachin Ilya V. ¹ , Panova Maria V. ¹ , Zinin Alexander I. ¹ , Malyshev Oleg R. ¹ , Kolotyrkina Natalya G. ¹ , Kononov Leonid O. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky prosp. 47, 119991, Russian Federation.

We have found that the deacetylation of O-acetylated pyranose glyco-oxazoline, derived from N-acetyl-d-glucosamine, using MeONa or other bases (Et3N, K2CO3) in MeOH, selectively gives the expected pyranose triol at 20 °C. In contrast, at 60 °C, a previously unknown, thermodynamically favored furanose isomer of the glyco-oxazoline triol is formed. Isomeric O-acetylated pyranose glyco-oxazolines, derived from N-acetyl-d-galactosamine or N-acetyl-d-mannosamine, also afford furanose isomers of the corresponding glyco-oxazoline triols upon treatment with MeONa in MeOH at 60 °C. The obtained unprotected furanose glyco-oxazoline with gluco-configuration was transformed into O-acetylated furanose gluco-oxazoline. The ability to prepare (un)protected furanose glyco-oxazolines opens a novel pathway to the underexplored furanose forms of glyco-oxazolines bearing various O-protective groups.

Romanyuk M.A. , Myachin I.V. , Panova M.V. , Zinin A.I. , Malyshev O.R. , Kolotyrkina N.G. , Kononov L.O.
Unexpected formation of furanose form during deacetylation of pyranose glyco-oxazolines
Carbohydrate Research. 2026. V.559. 109761 . DOI: 10.1016/j.carres.2025.109761 WOS Scopus OpenAlex

Web of science:	WOS:001629456400002
Scopus:	2-s2.0-105022635746
OpenAlex:	W4416416577

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