91382-84-2

Upstream product

• 91382-82-0 (+/-)-(1α,2β,3α,5α)-3-amino-5-(hydroxymethyl)-1,2-cyclopentanediol 
• 78738-50-8 (+/-)-4α-acetamido-2α,3β-dihydroxy-1α-cyclopentanemethanol 
• 61865-51-8 (1α,2α,3α,4α)-4-acetamido-2,3-epoxycyclopentylmethyl acetate 
• 91382-83-1 (+/-)-4α-<(5-amino-6-chloro-4-pyrimidinyl)amino>-2α,3β-dihydroxy-1α-cyclopentanemethanol 
• 38110-76-8 (+-)-cis-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one 
• 694-98-4 norborn-5-en-2-one 

Relevant academic research and scientific papers

The Ring Opening of Cyclopentene Oxides by Pyrimidines and Purines as a Pathway to Carbocyclic Nucleoside Analogues

Various carbocyclic nucleosides with xylo-configuration have been synthesized using ring opening of 5-O-acetyl-1,2-anhydro-3-O-benzylcarba-α-DL-xylo-pentofuranose (6) by thymine, uracil, 4-N-benzoylcytosine, adenine, 6-N-benzoyladenine, and 2-amino-6-chloropurine in alkaline medium. For this purpose, the use of triethylaluminum is introduced into carbanucleoside chemistry. The new method proved to be superior over the application of sodium hydride and potassium or caesium carbonate.

Carbocyclic analogues of xylofuranosylpurine nucleosides. Synthesis and antitumor activity

(±)-4α-Amino-2α,3β-dihydroxy-1α-cyclopentanemethanol (6), the carbocyclic analogue of xylofuranosylamine, was synthesized from the previously reported 4α-acetamido-2α,3α-epoxycyclopentane-1α-methanol. Amine 6 was converted to (±)-4α-[(5-amino-6-chloro-4-pyrimidinyl)amino]-2α,3β-dihydroxy-1α-cyc lopentanemethanol (7) by condensation with 5-amino-4,6-dichloropyrimidine. From 7, the carbocyclic analogues of xylofuranosyladenine and xylofuranosyl-8-azaadenine were prepared. In contrast to 9-β-D-xylofuranosyladenine and its 8-aza analogue, the corresponding carbocyclic nucleosides were resistant to deamination by adenosine deaminase. The carbocyclic 8-aza derivative exhibited significant in vivo antitumor activity which varied according to treatment schedule.