Optimization of Azidophenylselenylation of Glycals for the Efficient Synthesis of Phenyl 2-Azido-2-Deoxy-1-Selenoglycosides: Solvent Control

Optimization of Azidophenylselenylation of Glycals for the Efficient Synthesis of Phenyl 2-Azido-2-Deoxy-1-Selenoglycosides: Solvent Control Full article

Journal

Molecules
ISSN: 1420-3049

Output data

Year: 2026, Volume: 31, Number: 1, Article number : 54, Pages count : DOI: 10.3390/molecules31010054

Authors

Komarova Bozhena S. ¹ , Belova Olesia V. ¹ , Volkov Timur M. ¹ , Yashunsky Dmitry V. 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, Moscow 119991, Russia

Funding (3)

1	N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences
2
3

Azidophenylselenylation (APS) of glycals is a straightforward transformation for preparing phenylseleno 2-azido-2-deoxy derivatives, which are useful blocks in the synthesis of 2-amino-2-deoxy-glycoside-containing oligosaccharides. However, the previously developed APS methods employing the CH2Cl2 as solvent, Ph2Se2-PhI(OAc)2 (commonly known as BAIB), and a source of N3− are still not universal and show limited efficiency for glycals with gluco- and galacto-configurations. To address this limitation, we revisited both heterogeneous (using NaN3) and homogeneous (using TMSN3) APS approaches and optimized the reaction conditions. We found that glycal substrates with galacto- and gluco-configurations require distinct conditions. Galacto-substrates react relatively rapidly, and their conversion depends mainly on efficient azide-ion transfer into the organic phase, which is promoted by nitrile solvents (CH3CN, EtCN). In contrast, for the slower gluco-configured substrates, complete conversion requires a non-polar solvent still capable of azide-ion transfer, such as benzene. These observations were applied to the optimized synthesis of phenylseleno 2-azido-2-deoxy derivatives of d-galactose, d-glucose, l-fucose, l-quinovose, and l-rhamnose.

Komarova B.S. , Belova O.V. , Volkov T.M. , Yashunsky D.V. , Nifantiev N.E.
Optimization of Azidophenylselenylation of Glycals for the Efficient Synthesis of Phenyl 2-Azido-2-Deoxy-1-Selenoglycosides: Solvent Control
Molecules. 2026. V.31. N1. 54 . DOI: 10.3390/molecules31010054 WOS Scopus OpenAlex

Submitted:	Oct 27, 2025
Published online:	Dec 23, 2025

Web of science:	WOS:001657550800001
Scopus:	2-s2.0-105027105431
OpenAlex:	W7116962982

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