Synthesis of glycosides of 1H-Pyrazolo[3,4-b]pyridin-3(2H)-ones

A number of new fluorinated and non-fluorinated glycosides of 1H-pyrazolo[3,4-b]pyridin-3(2H)-ones were synthesized by direct attachment of the carbohydrate moiety to the heterocycle using the silyl Hilbert-Jones glycosylation method. The products were obtained in good to excellent yields and with v...

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Bibliographic Details
Published inTetrahedron Vol. 76; no. 44; pp. 131522 - 131551
Main Authors Supe, Linda, Hein, Martin, Iaroshenko, Viktor O., Villinger, Alexander, Langer, Peter
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 30.10.2020
Elsevier
Subjects
Chemistry
Chemistry, Organic
Cyclization
Glycosylation
Heterocycles
Organofluorine compounds
Physical Sciences
Regioselectivity
Science & Technology
Heterocycles
Glycosylation
Organofluorine compounds
Cyclization
Regioselectivity
DESIGN
ANALOGS
ADENOSINE
POTENT
INHIBITORS
STIMULATORS
ANTAGONISTS
ACETATE
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Summary:A number of new fluorinated and non-fluorinated glycosides of 1H-pyrazolo[3,4-b]pyridin-3(2H)-ones were synthesized by direct attachment of the carbohydrate moiety to the heterocycle using the silyl Hilbert-Jones glycosylation method. The products were obtained in good to excellent yields and with very good anomeric stereoselectivity. The starting 1H-pyrazolo[3,4-b]pyridin-3(2H)-ones were prepared by regioselective cyclization of 1,3-dicarbonyl compounds with electron-rich heterocycles containing an enamine functionality. [Display omitted] •The first glycosides of 1H-pyrazolo[3,4-b]pyridin-3(2H)-ones were prepared.•The reactions proceed with excellent regioselectivity.•The stereochemistry of the products was studied in detail.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2020.131522