Synthesis of 2-S-dioxo isosteres of purine and pyrimidine nucleosides. I. Alkyl and glycosyl derivatives of 3,5-diamino-4H-1,2,6-thiadiazine 1,1-dioxide |
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Authors: | P. Fern ndez Resa,M. Stud |
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Affiliation: | P. Fernández Resa,M. Stud |
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Abstract: | Preparation of alkyl and glycosyl derivatives of 3,5-diamino-4H-1,2,6-thiadiazine 1,1-dioxide (1) is described. Reaction of 1 with dimethyl sulfate gave the 4-methyl and 2,4-dimethyl derivatives. With benzyl chloride and allyl bromide C-4 substituted compounds were obtained. Reaction of the disilyl derivative of 1 with either 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide or 1,2,3,4,6-penta-O-acetyl-β-D-glucopyranose in the presence of Friedel-Crafts catalysts afforded the α and β anomers of the N-2 nucleoside and the β-O-glucoside. When the reaction was performed with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose, a β-C-glycoside and the α and β anomers of the N-2 nucleoside were obtained. The structure of the corresponding nucleosides were elucidated by 1H nmr and uv by comparing the latter with those of the alkyl derivatives. |
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