648414-60-2

Upstream product

• 191480-69-0 (3R,4S)-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]cyclopent-1-ene 
• 39939-07-6 5-(benzyloxymethyl)cyclopentadiene 
• 110567-21-0 (1S,2R)-2-(benzyloxymethyl)-1-hydroxy-3-cyclopentene 
• 3587-60-8 Benzyloxymethyl chloride 
• 100-39-0 benzyl bromide 
• 60410-16-4 (1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate 
• 542-92-7 cyclopenta-1,3-diene 

Downstream Products

• 892409-72-2 1-{(1S,2R,3S)-3-(benzyloxy)-2-[(benzyloxy)methyl]cyclopentyl}-5-methylpyrimidine-2,4(1H,3H)-dione 

Relevant academic research and scientific papers

Synthesis and biological evaluation of phosphoramidate prodrugs of two analogues of 2-deoxy-d-ribose-1-phosphate directed to the discovery of two carbasugars as new potential anti-HIV leads

2-Deoxy-α-d-ribose-1-phosphate is of great interest as it is involved in the biosynthesis and/or catabolic degradation of several nucleoside analogues of biological and therapeutic relevance. However due to the lack of a stabilising group at its 2-position, it is difficult to synthesize stable prodrugs of this compound. In order to overcome this lack of stability, the synthesis of carbasugar analogues of 2-deoxyribose-1-phosphate was envisioned. Herein the preparation of a series of prodrugs of two carbocyclic analogues of 2-deoxyribose-1-phosphate using the phosphoramidate ProTide technology, along with their biological evaluation against HIV and cancer cell proliferation, is reported.

The synthesis of possible transition state analogue inhibitors of thymidine phosphorylase

The synthetically challenging SN2 transition state mimic for thymidine phosphorylase, along with its phosphonate analogue, were synthesised via a modified Corey-Link reaction in good overall yields and ensuring the correct stereochemical outcome.

Divergent synthesis and biological evaluation of carbocyclic α-, iso- and 3′-epi-nucleosides and their lipophilic nucleotide prodrugs

A new divergent approach towards carbocyclic α-, iso- and 3′-epi-nucleosides starting from enantiomerically pure (1S,2R)-2-benzyloxymethylcyclopent-3-enol (5) is described. In the key step, isomeric cyclopentanols were condensed with a N3-protected pyrimi

New convergent synthesis of carbocyclic nucleoside analogues

Two convergent approaches towards the synthesis of carbocyclic nucleoside analogs will be described. Both approaches start from the stereochemically pure cyclopentenol 8 that has been prepared enantioselectively from an alkylated cyclopentadiene. Using these approaches, carbocyclic analogues of dT, FdU and BVdU have been prepared. Moreover, the conversion into the cycloSalpronucleotide and the corresponding nucleotide will be presented for one example.