Selective Acetalization in Pyridine: A Sustainable 5′-O-(2-Methoxypropyl) Protecting Group in the Synthesis of Nucleic Acid Analogs

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dc.contributor.authorSaari, Verneri
dc.contributor.authorEerola, Aino
dc.contributor.authorOra, Mikko
dc.contributor.authorMolina, Alejandro Gimenez
dc.contributor.authorHorvath, Andras
dc.contributor.authorSanghvi, Yogesh S.
dc.contributor.authorVirta, Pasi
dc.contributor.organizationfi=lääkekehityksen kemia|en=Pharmaseutical Chemistry|
dc.contributor.organization-code1.2.246.10.2458963.20.93793350823
dc.converis.publication-id499676799
dc.converis.urlhttps://research.utu.fi/converis/portal/Publication/499676799
dc.date.accessioned2026-01-21T14:47:28Z
dc.date.available2026-01-21T14:47:28Z
dc.description.abstract<p>A mixture of 2-methoxypropene and an acid catalyst in pyridine results in an efficient 5 '-<i>O</i>-(methoxyisopropyl) (MIP) acetalization of nucleosides, including 2 '-deoxy, 2 '-OH, 2 '-<i>O</i>-methyl, 2 '-<i>O</i>-methoxyethyl (MOE) and 2 '-F-variants, in 44-77% isolated yields. For the reaction mechanism, we propose a pyridinium 2-methoxyprop-2-yl preassociation complex, which improves regioselectivity for the primary (5 '-OH) over secondary (2 '-OH and 3 '-OH) hydroxy groups. The developed protocol makes the 5 '-<i>O</i>-MIP-acetal an attractive protecting group for the sustainable synthesis of nucleosides and oligonucleotides in solution.</p>
dc.format.pagerange8251
dc.format.pagerange8256
dc.identifier.eissn1523-7052
dc.identifier.jour-issn1523-7060
dc.identifier.olddbid213703
dc.identifier.oldhandle10024/196721
dc.identifier.urihttps://www.utupub.fi/handle/11111/55811
dc.identifier.urlhttps://pubs.acs.org/doi/10.1021/acs.orglett.5c02400
dc.identifier.urnURN:NBN:fi-fe202601215861
dc.language.isoen
dc.okm.affiliatedauthorSaari, Verneri
dc.okm.affiliatedauthorOra, Mikko
dc.okm.affiliatedauthorVirta, Pasi
dc.okm.discipline116 Chemical sciencesen_GB
dc.okm.discipline116 Kemiafi_FI
dc.okm.internationalcopublicationinternational co-publication
dc.okm.internationalityInternational publication
dc.okm.typeA1 ScientificArticle
dc.publisherAMER CHEMICAL SOC
dc.publisher.countryUnited Statesen_GB
dc.publisher.countryYhdysvallat (USA)fi_FI
dc.publisher.country-codeUS
dc.publisher.placeWASHINGTON
dc.relation.doi10.1021/acs.orglett.5c02400
dc.relation.ispartofjournalOrganic Letters
dc.relation.issue30
dc.relation.volume27
dc.source.identifierhttps://www.utupub.fi/handle/10024/196721
dc.titleSelective Acetalization in Pyridine: A Sustainable 5′-O-(2-Methoxypropyl) Protecting Group in the Synthesis of Nucleic Acid Analogs
dc.year.issued2025

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