69434-52-2

Upstream product

• 74892-69-6 Methyl 2,3:5,6-di-O-isopropylidene-α-D-mannofuranoside 
• 50692-25-6 Methyl 2,3-O-isopropylidene-5,6-di-O-methanesulfonyl-α-L-mannofuranoside 
• 26255-72-1 (3aR,4S,6aR)-4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole 
• 7757-38-2 2,3;5,6-di-O-isopropylidene-D-gulonic acid γ-lactol 
• 27954-10-5 (S)-1-((3aR,4S,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethane-1,2-diol 
• 1187858-68-9 Methyl 2,3-O-isopropylidene-α-D-gulofuranoside 
• 5328-37-0 L-arabinose 
• 613-90-1 benzoyl cyanide 
• 40789-24-0 Toluene-4-sulfonic acid (R)-2-hydroxy-2-((3aR,4S,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethyl ester 
• 98-59-9 p-toluenesulfonyl chloride 
• 27954-10-5 Methyl 2,3-O-isopropylidene-α-L-gulofuranoside 
• 70831-51-5 (R)-1-((3aS,4R,6aS)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethane-1,2-diol 
• 55520-71-3 Methyl 5,6-di-O-benzoyl-2,3-O-isopropylidene-α-L-gulofuranoside 
• 84857-02-3 Methyl 6-O-benzoyl-2,3-O-isopropylidene-α-L-gulofuranoside 

Relevant academic research and scientific papers

SYNTHESIS OF EIGHT STEREOISOMERIC 5-(ADENIN-9-YL)-2,3,4-TRIHYDROXYPENTANOIC ACIDS

Condensation of 5-O-p-toluenesulfonyl-2,3-O-isopropylidene-D-ribonolactone (XIIIb) with sodium salt of adenine afforded compound XIV which on alkaline, followed by acid, hydrolysis gave the (2R,3R,4R)-isomer V.The (2S,3S,4S)-isomer VIII was prepared analogously from the L-ribonolactone derivative XVb via the adenine derivative XVI. Compound XVIIc was transformed by reaction with adenine into 6-(adenin-9-yl)-6-deoxy-D-glucose (XIX); similarly, 6-(adenin-9-yl)-6-deoxy-D-mannose (XXI) was prepared from the protected D-mannofuranoside XX.Oxidation of compounds XIX and XXI in alkaline medium afforded the (2S,3R,4R)-isomer VI, 1,2:3,4-Di-O-isopropylidene-D-galactopyranose (XXIIa) was transformed into 6-(adenin-9-yl)-6-deoxy-D-galactose (XXIIIb) which was oxidatively cleaved to give the (2S,3S,4R)-isomer VII.Methyl 5,6-di-O-methanesulfonyl-2,3-O-isopropylidene-D-mannofuranoside (XXVIb) was transformed into the reactive L-gulofuranoside derivative XXVIIe which on condensation with adenine and oxidative cleavage gave the (2S,3R,4S)-isomer IX.The (2R,3S,4R)-isomer XI was prepared analogously from the D-gulofuranose derivative XXXIb.Starting from L-mannose, the (2R,3S,3S)-derivative X was prepared via the 6-(adenin-9-yl)-6-deoxy-L-mannofuranoside derivative XXXc.Methyl 5-O-p-toluenesulfonyl-2,3-O-isopropylidene-L-lyxofuranoside XXXVb was transformed into 5-(adenin-9-yl)-5-deoxy-2,3-O-isopropylidene-L-lyxofuranose (XXXVII) which was oxidized to the lactone XXXVIII; this compound on successive alkaline and acid hydrolysis afforded the (2R,3R,4S)-isomer XII.