Compounds related to acyclovir. VI. Synthesis of optically active 1',2'-seconucleosides

I. P. Smirnov, S. V. Kochetkova, T. L. Tsilevich, A. A. Khorlin, B. P. Gottikh, V. L. Florentiev

V. A. Engelhardt Institute of Molecular Biology, Academy of Sciences of the USSR, Moscow

Abstract: A convenient method is suggested of synthesis of (3R, 4S)-, (3S, 4S)- and (3R/S, 4S/R) dihydroxy-3-hydroxymethyl-2-oxapentyl derivatives of thymine, cytosine, uracyl, adenine and guanine («full» acyclic analogues of nucleosides with C1'—C2' bond cleaved) by condensation of trimethylsilyl derivatives of nucleic bases (sodium salt in case of adenine) with (3R, 4R)-, (3S, 4S)- and (3R/S, 4S/R) -4,5-diacetoxy-3-acetoxymethyl-l-chloro-2-oxapentanes without catalyst followed by deacetylation.

Russian Journal of Bioorganic Chemistry 1990, 16 (10):1355-1361

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