DIOXOLANE NUCLEOSIDES AND THEIR PHOSPHONATE DERIVATIVES - SYNTHESIS AND HYDROLYTIC STABILITY



: EFIMTSEVA EV, MIKHAILOV SN, MESHKOV S, HANKAMAKI T, OIVANEN M, LONNBERG H

Publisher: ROYAL SOC CHEMISTRY

: 1995

Journal of the Chemical Society. Perkin transactions 1

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1

: J CHEM SOC PERK T 1

: 11

: 1409

: 1415

: 7

: 0300-922X

DOI: https://doi.org/10.1039/p19950001409


Several new nucleoside (12-15):and nucleoside phosphonate (27-30) analogues derived from (+/-)-cis-and -trans-2-hydroxymethyl-4-methyl-1,3-dioxolane have been prepared and their configurations assigned by H-1 NMR spectroscopy. First-order rate constants for the acid-catalysed hydrolysis of the dioxolane ring have been determined at different hydronium ion concentrations. The phosphonate group accelerates the hydrolysis at pH > 2 by 2 orders of magnitude, while at pH < 1 the hydrolytic stabilities of the nucleoside analogues and their phosphonate derivatives are comparable. The possible reasons for this rate-enhancement are discussed on the basis of the reaction mechanism.



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