181868-33-7

Upstream product

• 4157-02-2 cis 2-cyclopentene 1,4-dibenzoate 
• 87-42-3 6-chloropurine 
• 98-88-4 benzoyl chloride 
• 158799-93-0 (1S,4R)-4-(6-chloro-9H-purin-9-yl)cyclopent-2-enol 
• 93-97-0 benzoic acid anhydride 
• 60410-16-4 (1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate 

Downstream Products

• 188907-60-0 (1'R,4'S)-1'-(6-chloropurin-9-yl)-4'-phenylsulfonyl(nitro)methyl-cyclopent-2'-ene 
• 536741-60-3 (1'R,4'S)-1'-(6-chloro-9H-purin-9-yl)-4'-[nitro(phenylsulfonyl)-[13C]methyl]cyclopent-2'-ene 
• 156407-85-1 2',3'-diepi-neplanocin 
• 188907-68-8 (3'R,4'R)-4'-(6-chloropurin-9-yl)-1'-methoxycarbonyl-3'-(p-nitrobenzoyl)oxy-cyclopent-1'-ene 
• 188907-61-1 (1'R,2'R,3'S,4'S)-1'-(6-chloropurin-9-yl)-2',3'-epoxy-4'-phenylsulfonyl(nitro)methyl-cyclopentane 
• 72877-50-0 neplanocin A 

Relevant academic research and scientific papers

Amino substituted derivatives of 5′-amino-5′-deoxy-5′- noraristeromycin

The potent antiviral potential of 5′-amino-5′-deoxy-5′- noraristeromycin (2) is limited by associated toxicity. To seek derivatives of 2 that circumvent this undesirable property, three amino substituted derivatives (acetyl, 3; formyl, 4; and methyl, 5) of 2 have been prepared in 4-7 steps from the same intermediate, (1S,4R)-4-(6-chloropurin-9-yl)cyclopent-2-en-1-ol (6). Key steps involved an improved Pd(0)-catalyzed allylic azidation and a novel Pd(0)-catalyzed allylic amidation. The three target compounds were evaluated against a large number of viruses and found to be inactive except for a very weak effect of 5 on human cytomegalovirus, varicella zoster virus, and Epstein-Barr virus. There was also no noteworthy cytotoxicity associated with the new derivatives. Thus, these results indicate variation of the cyclopentyl amine of 2 does not offer a means to improve upon its antiviral potential.

Synthesis of enantiomerically-pure [13C]aristeromycylcobalamin and its reactivity in dioldehydratase, glyceroldehydratase, ethanolamine ammonia-lyase and methylmalonyl-CoA mutase reactions

We describe a novel enantio-selective synthesis of aristeromycin, the carbocyclic analogue of adenosine. The seven-step synthesis is also suitable for the preparation of specifically-labelled [6′-13C]aristeromycin. Both the unlabelled and

Palladium-catalyzed enantioselective synthesis of carbanucleosides

A general strategy has been developed for enantioselective synthesis of diverse carbanucleosides. The key step is a Pd(0)-catalyzed enantioselective allylic amination of cis-3,5-dibenzoyloxycyclopent-2-ene 10a with the nucleobase. With guanine-derived nuc

An enantio- and diastereo-controlled synthesis of (-)neplanocin A and its 2,3-di-epi isomer

An enantioselective Pd catalyzed desymmetrization of cis-3,5-dibenzoyloxycyclopent-2-ene combined with a diastereoselective epoxidation provided a common intermediate that can bifurcate to form either (-)-neplanocin A or its 2,3-di-epi isomer.

Eine kurze, enantioselektive Synthese von Carbanucleosiden

Keywords: Alkylierungen; Asymmetrische Katalyse; Carbanucleoside; Palladiumverbindungen