{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,12,23]],"date-time":"2025-12-23T16:33:06Z","timestamp":1766507586621,"version":"3.48.0"},"reference-count":51,"publisher":"MDPI AG","issue":"1","license":[{"start":{"date-parts":[[2025,12,23]],"date-time":"2025-12-23T00:00:00Z","timestamp":1766448000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100006769","name":"Russian Science Foundation","doi-asserted-by":"publisher","award":["19-73-30017-P"],"award-info":[{"award-number":["19-73-30017-P"]}],"id":[{"id":"10.13039\/501100006769","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>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\u2212 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.<\/jats:p>","DOI":"10.3390\/molecules31010054","type":"journal-article","created":{"date-parts":[[2025,12,23]],"date-time":"2025-12-23T14:27:47Z","timestamp":1766500067000},"page":"54","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Optimization of Azidophenylselenylation of Glycals for the Efficient Synthesis of Phenyl 2-Azido-2-Deoxy-1-Selenoglycosides: Solvent Control"],"prefix":"10.3390","volume":"31","author":[{"given":"Bozhena S.","family":"Komarova","sequence":"first","affiliation":[{"name":"Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, Moscow 119991, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Olesia V.","family":"Belova","sequence":"additional","affiliation":[{"name":"Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, Moscow 119991, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Timur M.","family":"Volkov","sequence":"additional","affiliation":[{"name":"Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, Moscow 119991, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Dmitry V.","family":"Yashunsky","sequence":"additional","affiliation":[{"name":"Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, Moscow 119991, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0727-4050","authenticated-orcid":false,"given":"Nikolay E.","family":"Nifantiev","sequence":"additional","affiliation":[{"name":"Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, Moscow 119991, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2025,12,23]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"e202511378","DOI":"10.1002\/ange.202511378","article-title":"Synthesis, Conformal Analysis, and Antibody Binding of Staphylococcus aureus Capsular Polysaccharide Type 5 Oligosaccharides","volume":"137","author":"Li","year":"2025","journal-title":"Angew. 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