ChemInform Abstract: A Convenient Route to 3′‐Deoxy‐α‐L‐ and 3′‐Deoxy‐β‐D‐ apionucleosides.

Abstract

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Nucleosides with Transposed Base or 4′-Hydroxymethyl Moieties and Their Corresponding Oligonucleotides

“…23,25 The D-and L-3′-deoxyapionucleosides 9a−e and 10a−c failed to inhibit DNA or RNA viruses (e.g., HIV-1, HIV-2, HSV-1, HSV-2, VV, and VSV) and, unlike their 2′-deoxy regiomers 6a−c, show no cytotoxicity. 26 Later Jung et al found 9b active against HSV-1(KOS) (MIC 50 = 39.6 μM) and 9e active against HSV-1 in two different cell lines, i.e., KOS and 2(G) (MIC 50 = 7.1 and 35.9 μM, respectively). 27,28 The cytidine congener 11 was shown to be inactive against HIV.…”

“…Barton–McCombie deoxygenation (BMD) is also a popular method to access 3-deoxyapio synthons. One such example is depicted in Scheme and engaged cyclic thionocarbonate 154 , readily available in four steps from the previously mentioned 2,3- O -isopropylidene- d -apio-β- d -furanose ( 151 ) . Although straightforward, this method lacked selectivity, providing a mixture of d - and l -furanosides 155 and 156 , which were separated by chromatography before Vorbrüggen-type base condensation.…”