The primary hydroxy group of ethyl 2,3-dideoxy-alpha-D-erythro-hex-2-enopyranoside (1) was selectively protected and the secondary hydroxy group was deoxygenated via the dithiocarbonate 3 from which ethyl 6-O-(4-methoxybenzoyl)-2,3,4-trideoxy-alpha-D-glycero-hex-2-eno pyranoside (4) and its regioisomer (5) were produced. These were converted into didehydro nucleosides by glycosylation of silylated heterocyclic bases in the presence of trimethylsilyl trifluoromethanesulfonate as catalyst. The configurations of the anomeric products were assigned by 1H-NMR analysis of the corresponding saturated compounds which were obtained by hydrogenation of the double bond in the carbohydrate moiety. The compounds 9a,b,d, 10a,b, 14a,b,e,f, and 15a,b,e,f did not show any significant activity against HIV or HSV-1.

3‐(6‐Alkylaminopurin‐9‐yl)‐2,3‐dideoxy‐D‐threo‐pentopyranoses 3 were prepared by condensation of unprotected 2‐deoxy‐D‐ribose (2) with N6‐alkyladenines 1 in a phosphorus pentoxide reagent mixture. Reduction of the pentoses 3 gave the corresponding 3‐(6‐alkylaminopurin‐9‐yl)‐2,3‐dideoxy‐D‐threo‐pentitols 4. The structures of 3 and 4 were determined by 13C nmr, 1H nmr and 2D 1H nmr (COSY).

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ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.