A1 Vertaisarvioitu alkuperäisartikkeli tieteellisessä lehdessä
Selective Acetalization in Pyridine: A Sustainable 5′-O-(2-Methoxypropyl) Protecting Group in the Synthesis of Nucleic Acid Analogs
Tekijät: Saari, Verneri; Eerola, Aino; Ora, Mikko; Molina, Alejandro Gimenez; Horvath, Andras; Sanghvi, Yogesh S.; Virta, Pasi
Kustantaja: AMER CHEMICAL SOC
Kustannuspaikka: WASHINGTON
Julkaisuvuosi: 2025
Lehti:: Organic Letters
Lehden akronyymi: ORG LETT
Vuosikerta: 27
Numero: 30
Aloitussivu: 8251
Lopetussivu: 8256
Sivujen määrä: 6
ISSN: 1523-7060
eISSN: 1523-7052
DOI: https://doi.org/10.1021/acs.orglett.5c02400
Verkko-osoite: https://pubs.acs.org/doi/10.1021/acs.orglett.5c02400
Rinnakkaistallenteen osoite: https://research.utu.fi/converis/portal/detail/Publication/499676799
A mixture of 2-methoxypropene and an acid catalyst in pyridine results in an efficient 5 '-O-(methoxyisopropyl) (MIP) acetalization of nucleosides, including 2 '-deoxy, 2 '-OH, 2 '-O-methyl, 2 '-O-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 '-O-MIP-acetal an attractive protecting group for the sustainable synthesis of nucleosides and oligonucleotides in solution.
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The financial support from the Doctoral Programme in Exact Scienses (EXACTUS) and University of Turku Foundation is acknowledged.
