J. Branalt et al., SYNTHESIS OF 5-BIS(HYDROXYMETHYL)-1,3-DIOXOLAN-2-YL]NUCLEOSIDES AS POTENTIAL INHIBITORS OF HIV, Journal of organic chemistry, 61(11), 1996, pp. 3599-3603
The synthesis of 1,3-dioxolan-2-ylnucleosides and related chemistry is
described. We have shown that 2-methoxy-1,3-dioxolane (6) reacts with
silylated thymine and trimethylsilyl triflate to give the acyclic for
mate ester 1-[2-(formyloxy)ethyl]thymine (8) rather than 1-(1,3-dioxol
an-2-yl)thymine (7). A tentative mechanism which could explain this re
sult is discussed. On the other hand, 2-methoxy-1,3-dioxolane 13c reac
ts with silylated bases to give 5-bis(hydroxymethyl)-1,3-dioxolan2-yl]
nucleosides, thus representing the first examples of this novel class
of compounds. The nature of the nucleobase and the hydroxyl protecting
groups was found to have great influence on the reaction and on the s
tability of the nucleosides. Compounds 16 and 18 were found to be inac
tive when tested for anti HIV-1 activity in vitro.