322390-91-0

Upstream product

• 2595-05-3 Diacetone D-glucose 
• 322390-89-6 3,5-Di-O-benzyl-1,2-O-isopropylidene-6-O-triphenylmethyl-3-C-vinyl-α-D-allofuranose 
• 322390-88-5 1,2-O-Isopropylidene-6-O-triphenylmethyl-3-C-vinyl-α-D-allofuranose 
• 51996-47-5 (3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-vinyltetrahydrofuro[2,3-d][1,3]-dioxol-6-ol 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 151426-71-0 1,2-di-O-isopropylidene-3-C-vinyl-β-D-allofuranose 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 124-63-0 methanesulfonyl chloride 
• 322390-90-9 Methyl 3,5-di-O-benzyl-3-C-vinyl-α-D-allofuranoside 

Downstream Products

• 322390-95-4 (1R,3R/S,4S,7R,10R,11R)-10,11-Dibenzyloxy-3-(thymin-1-yl)-2,5,8-trioxatricyclo[5.3.1.0^4,11]undecane 
• 322390-93-2 (1R,3R,4S,7R,10R,11R)-10,11-Dibenzyloxy-3-methoxy-2,5,8-trioxatricyclo[5.3.1.0^4,11]undecane 

Relevant academic research and scientific papers

Synthesis and NMR-analysis of tricyclic nucleosides

Two anomeric tricyclic nucleosides have been synthesised from diacetone-D-glucose using oxidation, stereoselective Grignard-addition of a vinyl-group, a stereoselective dihydroxylation followed by a tandem ring closing reaction, and finally a nucleobase coupling. The main β-configured product was examined and its configuration confirmed using NMR-spectroscopy in connection to ab initio calculations. The preferred conformation of this tricyclic nucleoside was described.

Tricyclic nucleosides derived from D-glucose. Synthesis and conformational behaviour

Two anomeric nucleosides with tricyclic carbohydrate moieties, 3 and 14, are synthesised in 11 steps from diacetone-D-glucose, taking advantage of a stereoselective Grignard reaction, a stereoselective dihydroxylation and a regioselective tandem ring-closing procedure. The configuration of 3 is confirmed by measuring the 3JHH coupling constants in connection with molecular modelling and ab initio calculations, as these exclude alternative tricyclic nucleoside structures. The conformational preference for 3 is described. The furanose ring is found to be in an O-4′-endo conformation and the γ torsion angle in the +ap range.