Regioselective O6-diphenylcarbamoylation of 7-deazaguanine derivatives via a stable intermediate 1-(diphenylcarbamoyl)-4-(dimethylamino)pyridinium chloride

[Display omitted] •O6-Selective diphenylcarbamoylation of N2-acyl-7-deazaguanine derivatives.•1-(Diphenylcarbamoyl)-4-(dimethylamino)pyridinium chloride (DPC-DMAP).•Stability of the active species DPC-DMAP is the key to selectivity. Regioselective protection at the O6-position of N2-pivaloyl-7-deaza...

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Bibliographic Details
Published in:Tetrahedron letters 2020-07, Vol.61 (28), p.152085, Article 152085
Main Authors: Oka, Natsuhisa, Nakano, Koki, Fukuta, Akane, Ando, Kaori
Format: Article
Language:English
Subjects:
7-Deazaguanine
Diphenylcarbamoyl
DMAP
Regioselective
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Summary:[Display omitted] •O6-Selective diphenylcarbamoylation of N2-acyl-7-deazaguanine derivatives.•1-(Diphenylcarbamoyl)-4-(dimethylamino)pyridinium chloride (DPC-DMAP).•Stability of the active species DPC-DMAP is the key to selectivity. Regioselective protection at the O6-position of N2-pivaloyl-7-deazaguanine derivatives was achieved by using diphenylcarbamoyl chloride (DPC-Cl) and DMAP. The adduct of DPC-Cl and DMAP, 1-(diphenylcarbamoyl)-4-(dimethylamino)pyridinium chloride (DPC-DMAP), was isolated and fully characterized. DPC-DMAP is a stable, crystalline compound which is precipitated at ambient temperatures to stall the reaction. Upon heating, it reacts with the 6-carbonyl oxygen of N2-pivaloyl-7-deazaguanine derivatives selectively, enabling a completely regioselective reaction.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2020.152085