173346-41-3

Upstream product

• 174171-97-2 (1'R,2'R,3'S,4'R)-4'-(6-aminopurin-9-yl)-1'-hydroxymethyl-2',3'-O-isopropylidenecyclopentane-2',3'-diol 
• 98-59-9 p-toluenesulfonyl chloride 
• 67814-68-0 2,3-O-isopropylidene-D-ribofuranose 
• 115509-13-2 (3aR,6aR)-2,2-Dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one 
• 155934-55-7 (4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolane-4-carbaldehyde 
• 186540-95-4 ((3aR,4R,6R,6aS)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methanol 
• 683276-43-9 (4R,5R)-1-(2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)prop-2-en-1-ol 
• 888956-47-6 6-Chloro-9-((3aS,4R,6R,6aR)-2,2-dimethyl-6-vinyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-9H-purine 
• 698999-23-4 (3aS,4S,6R,6aR)-2,2-dimethyl-6-vinyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol 
• 698999-19-8 (3aR,6R,6aR)-2,2-dimethyl-6-vinyltetrahydro-4H-cyclopenta[d]-[1,3]-dioxol-4-one 
• 683276-44-0 (4R,5S)-4,5-O-isopropylidenecyclopenten-1-ol 

Downstream Products

• 1053260-67-5 (S)-4-(2-{[(3aR,4R,6R,6aS)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ylmethyl]-methyl-amino}-ethyl)-5-oxo-oxazolidine-3-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

Preparation of carbocyclic S-adenosylazamethionine accompanied by a practical synthesis of (-)-aristeromycin

For the preparation of a carbocyclic nitrogen analogue of S-adenosylmethionine (carba-AdoazaMet, 4), a practical synthesis of (-)-aristeromycin (7) has been developed using variations of literature procedures. This approach called for a stereospecific synthesis of (3aR,6aR)-2,2-dimethyl-3a, 6a-dihydrocyclopenta[1,3]dioxol-4-one ((4R, 5R)-4,5-O-isopropylidene-2-cyclopentenone) (8), which was achieved by modifying reported procedures from D-(-)-ribose.

Synthesis of homologated halovinyl derivatives from aristeromycin and their inhibition of human placental S-adenosyl-L-homocysteine hydrolase

Moffatt oxidation of 2',3'-O-isopropylidenearisteromycin (1a) and treatment of the 5'-carboxaldehyde with [(p- tolylsulfonyl)methylene]triphenylphosphorane gave the homologated vinylsulfone 2. Treatment of 2 with tributylstannane/AIBN gave the (E/Z)- vinylstannanes which were converted into the E and Z fluoro- and iodovinyl analogs. Chain extension via the 5'-cyano-5'-deoxy derivative 10a gave the 6'-carboxaldehyde of homoaristeromycin. S-Adenosyl-L-homocysteine hydrolase was strongly inhibited by the fluorovinyl, 5b, and iodovinyl, 4b and 7b, compounds, and time-dependent kinetics were observed [1-2 μM (K(i)) and 0.1- 0.2 min-1 (k(inact))]. The mechanism of inactivation was shown to involve addition of water at the vinyl 5' or 6' carbons with elimination of halide.