Temperature controlled stereoselectivity in the synthesis of 5-halo-2′-deoxyuridine derivatives

[Display omitted] A series of α- and β-5-halo-2′-deoxyuridine derivatives were prepared with high anomeric selectivity using the conventional silylbase glycosylation method and taking advantage of the 3′-O-(N-acetyl)glycyl protection group and temperature control. Reactions performed at −7°C gave as...

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Bibliographic Details
Published in:Tetrahedron letters 2015-10, Vol.56 (43), p.5950-5953
Main Authors: Lagerwall, Tom, Heinonen, Petri, Oivanen, Mikko
Format: Article
Language:English
Subjects:
5-Halouracil
Deoxynucleoside
Glycosylation
Silylbase method
Stereoselectivity
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Summary:[Display omitted] A series of α- and β-5-halo-2′-deoxyuridine derivatives were prepared with high anomeric selectivity using the conventional silylbase glycosylation method and taking advantage of the 3′-O-(N-acetyl)glycyl protection group and temperature control. Reactions performed at −7°C gave as much as 87% of the β-anomers, while an overnight reaction at 30°C gave up to 95% of the α-anomers.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2015.09.061