592533-90-9

Usage

Uses

Used in Pharmaceutical Industry:
(3aS,4R,6S,6aR)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-ol is used as a reagent for the synthesis of (3S,4R,5S)-(+)-3-amino-4,5-dihydroxycyclopentene. This synthesized compound serves as a chiral synthon, which is a crucial building block in the development of carbocyclic nucleosides. These nucleosides have significant potential in the treatment of various diseases, including viral infections and cancer, due to their unique properties and ability to interfere with the replication of genetic material in cells.

Upstream product

• 592533-89-6 (1S,2R,6R,7R)-4,4-Dimethyl-3,5,8-trioxa-9-aza-tricyclo[5.2.1.0^2,6]decane 
• 701917-18-2 2-((1S,4R)-4-hydroxycyclopent-2-en-1-yl)isoindoline-1,3-dione 
• 204912-92-5 (1S,4R)-4-hydroxy-2-cyclopenten-1-yl diethyl phosphate 
• 160167-61-3 (1R,4S)-N--2,3-oxazabicyclo<2.2.1>hept-5-ene 
• 542-92-7 cyclopenta-1,3-diene 

Relevant academic research and scientific papers

An enantioselective synthesis of the cyclopentene fragment of nucleoside Q

An enantioselective synthesis of (3S,4R,5S)-(+)-3-amino-4,5-dihydroxycyclopentene, a segment of nucleoside Q and Q base, is reported utilizing an amino acid-derived acylnitroso Diels-Alder cycloaddition.

L-deaza-5'-noraisteromycin.

(+/-)-1-Deazaaristeromycin (4) has been reported to be an inactivator of S-adenosylhomocysteine (AdoHcy) hydrolase and, as a consequence, to affect S-adenosylmethionine (AdoMet) mediated macromolecular biomethylations. To extend this to our program focused on 5'-noraristeromycin derivatives as inhibitors of the same hydrolase enzyme as potential antiviral agents, both enantiomers of 1-deaza-5'-noraristeromycin (5 and 20) have been prepared. Compounds 5 and 20 were evaluated against the following viruses: vaccinia, cowpox, monkeypox, Ebola, herpes simplex type 1 and 2, human cytomegalovirus, Epstein Barr, varicella zoster, hepatitis B, hepatitis C, HIV-1 and HIV-2, adenovirus type 1, measles, Pichinde, parainfluenza type 3, influenza A (H1N1 and H3N2), influenza B, Venezuelan equine encephalitis, rhinovirus type 2, respiratory syncytial, yellow fever, and West Nile. No activity was found nor was there any cytotoxicity to the viral host cells.

Rapid syntheses of either enantiomer of important carbocyclic nucleoside precursors

The syntheses of both enantiomers of aminocyclopentanetriol 1, a versatile carbocyclic nucleoside precursor, is reported utilizing an amino acid-derived acylnitroso Diels-Alder cycloaddition. The sequence is practical and proceeds in an overall yield of 36% from the D-alanine-derived hydroxamic acid. (C) 2000 Elsevier Science Ltd.