107325-67-7

Usage

InChI:InChI=1/C11H14N2O5/c12-11(17)6-1-5(2-13-3-6)10-9(16)8(15)7(4-14)18-10/h1-3,7-10,14-16H,4H2,(H2,12,17)/t7-,8-,9-,10+/m1/s1

Upstream product

• 115078-62-1 5-(2,3:4,5-di-O-isopropylidene-1-O-mesyl-D-altro-pentitol-1-yl)nicotinamide 
• 107325-66-6 methyl 5-(2,4:3,5-di-O-benzylidene-1-O-mesyl-D-pentitol-1-yl)nicotinamide 
• 625-92-3 3,5-dibromopyridine 
• 115078-49-4 1-(3-cyanopyridin-5-yl)-2,3-O-isopropylidene-5-O-(tetrahydropyran-2-yl)-β-D-ribofuran-1-ulose 
• 115078-56-3 5-(2,3:4,5-di-O-isopropylidene-D-altro-pentitol-1-yl)-3-cyanopyridine 
• 115078-52-9 5-<2,3-O-isopropylidene-5-O-(tetrahydropyran-2-yl)-D-altro-pentitol-1-yl>-3-cyanopyridine 
• 115078-58-5 5-(2,3:4,5-di-O-isopropylidene-D-altro-pentitol-1-yl)nicotinamide 
• 115078-54-1 5-(2,3-O-isopropylidene-D-altro-pentitol-1-yl)-3-cyanopyridine 
• 31858-77-2 2,3-O-isopropylidene-5-O-(tetrahydropyranyl)-D-ribonolactone 
• 107325-63-3 methyl 5-(2,4:3,5-di-O-benzylidene-D-pentitol-1-yl)nicotinate 
• 107325-64-4 5-(2,4:3,5-di-O-benzylidene-D-pentitol-1-yl)nicotinamide 
• 139258-55-2 5-[((2R,4S,4aR,6R,8aR)-2,6-Diphenyl-tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxin-4-yl)-hydroxy-methyl]-nicotinic acid 
• 107325-62-2 5-(2,4:3,5-di-O-benzylidene-D-pentitol-1-yl)-3-bromopyridine 
• 107436-58-8 2,4:3,5-di-O-benzylidene-D-aldehydo-ribose 

Relevant academic research and scientific papers

Efficient Synthesis of 5-(β-D-Ribofuranosyl)nicotinamide and Its α-Isomer

Condensation of 2,3-O-isopropylidene-5-O-(tetrahydropyranyl)-D-ribonolactone (3) with 3-cyano-5-lithiopyridine afforded 1-(3-cyanopyridin-5-yl)-2,3-O-isopropylidene-5-O-(tetrahydropyranyl)-β-D-ribofuran-1-ulose (5a), which was reduced with NaBH4 to a 1:1 allo/altro mixture of 5--3-cyanopyridine (7a).The isomers were chromatographically separated.Treatment of allo-7a with TsOH/MeOH gave 5-(2,3-O-isopropylidene-D-allo-pentitol-1-yl)-3-cyanopyridine (allo-8a), which was acetonated to give 5-(2,3:4,5-di-O-isopropylidene-D-allo-pentitol-1-yl)-3-cyanopyridine (allo-9a).Mesylation of allo-9a to allo-10 followed by acid hydrolysis with CF3CO2H/CHCl3 afforded 5-(α-D-ribofuranosyl)-3-cyanopyridine (11a).The β-isomer 1a was synthesized in a similar manner from altro-7a.Inversion of the configuration at the C-1 position of 6-(2,3:4,5-di-O-isopropylidene-D-allo-pentitol-1-yl)-2-bromopyridine (allo-9b) into the corresponding altro isomer altro-9b was achieved albeit in modest yield (24percent) by mesylation of allo-9b to allo-10b followed by treatment with potassium superoxide.Interconversion of altro-9a or -9b into the corresponding allo derivatives was readily achieved in excellent yield by oxidation with CrO3/pyridine/Ac2O to the corresponding keto intermediates 19 followed by borohydride reduction.Treatment of the 1-O-mesylate allo-10b with NaN3 in DMF afforded the corresponding 1-azido-1-deoxy derivative (17).Similar treatment of the 1-O-triflyl derivatives allo-15a,b with NaN3 or NaOAc in DMF surprisingly afforded allo-9a,b in good yield.