69435-65-0Relevant academic research and scientific papers
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
Resa, P. Fernandez,Stud, M.
, p. 27 - 30 (2007/10/02)
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.
