78738-50-8

Upstream product

• 126958-90-5 (1S,3R,4R)-4-Acetylamino-2,3-dihydroxy-cyclopentanecarboxylic acid methyl ester 
• 126958-90-5 (1R,3S,4S)-4-Acetylamino-2,3-dihydroxy-cyclopentanecarboxylic acid methyl ester 
• 108-24-7 acetic anhydride 
• 61865-51-8 (1α,2α,3α,4α)-4-acetamido-2,3-epoxycyclopentylmethyl acetate 
• 61865-49-4 ester methylique de l'acide (acetamido-cis-4)-cyclopentene-2-carboxylique 
• 69919-17-1 methyl (+)-(1R,4S)-4-acetamido-cyclopent-2-ene carboxylate 
• 127061-46-5 methyl (+)-cis-4-acetamidocyclopent-2-enecarboxylate 
• 112531-51-8 (-)-(1S,4R)-4-(acetylamino)-2-cyclopentene-1-carboxylic acid 

Downstream Products

• 91382-84-2 (+/-)-4α-adenin-9-yl-2α,3β-dihydroxy-1α-cyclopentanemethanol 
• 91382-82-0 (+/-)-(1α,2β,3α,5α)-3-amino-5-(hydroxymethyl)-1,2-cyclopentanediol 
• 50619-37-9 (+)-(1S,2R,3S,4S)-4-amino-2,3-dihydroxy-1-hydroxymethyl cyclopentane 
• 50619-37-9 (-)-(1R,2S,3R,4R)-4-amino-2,3-dihydroxy-1-hydroxymethyl cyclopentane 
• 85026-59-1 (-)-(1R,2R,3S,4R)-4-amino-2,3-dihydroxy-1-(hydroxymethyl)cyclopentane 

Relevant academic research and scientific papers

Biocatalytical Transformations- VI. The 4-Acetamido-cyclopent-2-ene Carboxylate Route Revisited: Synthesis of (+)- and (-)-Aristeromycin

Enantiomerically pure (+)-as well as (-)-aristeromycin can be synthesized starting from (+)- or (-)-butyl (or hexyl) 4-acetamido-cyclopent-2-ene carboxylate; these carboxylates are easily obtained from their corresponding racemates by hydrolysis with the lipase from Candida rugosa.

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.