A1 Refereed original research article in a scientific journal
SYNTHESIS AND PHYSICOCHEMICAL PROPERTIES OF DIOXOLANE NUCLEOSIDE ANALOGS
Authors: EFIMTSEVA EV, MIKHAILOV SN, MESHKOV SV, LONNBERG H
Publisher: MUNKSGAARD INT PUBL LTD
Publication year: 1992
Journal: Acta Chemica Scandinavica
Journal name in source: ACTA CHEMICA SCANDINAVICA
Journal acronym: ACTA CHEM SCAND
Volume: 46
Issue: 11
First page : 1122
Last page: 1126
Number of pages: 5
ISSN: 0904-213X
DOI: https://doi.org/10.3891/acta.chem.scand.46-1122
Abstract
Four novel nucleoside analogues, viz. the cis and trans isomers of 4-hydroxymethyl-2(uracil-1-ylmethyl)-1,3-dioxolane and 2-(adenin-9-ylmethyl)-4-hydroxymethyl-1,3-dioxolane, have been prepared. Alkylation of the sodium salts of uracil and adenine with 4-benzoyloxymethyl-2-bromomethyl-1,3-dioxolane, separation of the resulting cis and trans isomers by adsorption and reversed-phase chromatography, and deprotection with methanolic ammonia yielded the desired analogues of 2',3'-dideoxyribo-nucleosides. The structures of the products were verified by NMR spectroscopy, and the kinetics of their acid-catalyzed hydrolysis were studied.
Four novel nucleoside analogues, viz. the cis and trans isomers of 4-hydroxymethyl-2(uracil-1-ylmethyl)-1,3-dioxolane and 2-(adenin-9-ylmethyl)-4-hydroxymethyl-1,3-dioxolane, have been prepared. Alkylation of the sodium salts of uracil and adenine with 4-benzoyloxymethyl-2-bromomethyl-1,3-dioxolane, separation of the resulting cis and trans isomers by adsorption and reversed-phase chromatography, and deprotection with methanolic ammonia yielded the desired analogues of 2',3'-dideoxyribo-nucleosides. The structures of the products were verified by NMR spectroscopy, and the kinetics of their acid-catalyzed hydrolysis were studied.
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