SYNTHESIS AND PHYSICOCHEMICAL PROPERTIES OF DIOXOLANE NUCLEOSIDE ANALOGS



: EFIMTSEVA EV, MIKHAILOV SN, MESHKOV SV, LONNBERG H

Publisher: MUNKSGAARD INT PUBL LTD

: 1992

Acta Chemica Scandinavica

ACTA CHEMICA SCANDINAVICA

: ACTA CHEM SCAND

: 46

: 11

: 1122

: 1126

: 5

: 0904-213X

DOI: https://doi.org/10.3891/acta.chem.scand.46-1122


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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