91382-82-0

Upstream product

• 69919-17-1 methyl (+)-(1R,4S)-4-acetamido-cyclopent-2-ene carboxylate 
• 112531-51-8 (-)-(1S,4R)-4-(acetylamino)-2-cyclopentene-1-carboxylic acid 
• 127061-46-5 methyl (+)-cis-4-acetamidocyclopent-2-enecarboxylate 
• 78738-50-8 (+/-)-4α-acetamido-2α,3β-dihydroxy-1α-cyclopentanemethanol 
• 61865-51-8 (1α,2α,3α,4α)-4-acetamido-2,3-epoxycyclopentylmethyl acetate 
• 126958-90-5 (1S,3R,4R)-4-Acetylamino-2,3-dihydroxy-cyclopentanecarboxylic acid methyl ester 
• 61865-49-4 ester methylique de l'acide (acetamido-cis-4)-cyclopentene-2-carboxylique 
• 13190-81-3 N-((1R,3S,4R)-2,3-Dihydroxy-4-hydroxymethyl-cyclopentyl)-acetamide 
• 126958-90-5 (1R,3S,4S)-4-Acetylamino-2,3-dihydroxy-cyclopentanecarboxylic acid methyl ester 
• 13190-81-3 N-((1S,3R,4S)-2,3-Dihydroxy-4-hydroxymethyl-cyclopentyl)-acetamide 

Downstream Products

• 108742-11-6 (+/-)-(1α,2β,3α,5α)-3-(5-amino-7-chloro-3H-1,2,3-triazolo<4,5-d>pyrimidin-3-yl)-5-(hydroxymethyl)-1,2-cyclopentanediol 
• 108742-13-8 (+/-)-(1α,2β,3α,5α)-3-(5,7-diamino-3H-1,2,3-triazolo<4,5-d>pyrimidin-3-yl)-5-(hydroxymethyl)-1,2-cyclopentanediol 
• 108742-08-1 (+/-)-(1α,2β,3α,5α)-3-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)-1,2-cyclopentanediol 
• 108742-10-5 (+/-)-(1α,2β,3α,5α)-3-(2,6-diamino-9H-purin-9-yl)-5-(hydroxymethyl)-1,2-cyclopentanediol 
• 108742-06-9 (+/-)-(1α,2β,3α,5α)-3-<<2-amino-6-chloro-5-<(4-chlorophenyl)azo>-4-pyrimidyl>amino>-5-(hydroxymethyl)-1,2-cyclopentanediol 
• 108742-12-7 (+/-)-5-amino-3,6-dihydro-3-<(1α,2β,3α,5α)-2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl>-7H-1,2,3-triazol<4,5-d>pyrimidin-7-one 
• 108742-09-2 (+/-)-2-amino-1,9-dihydro-9-<(1α,2β,3α,5α)-2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl>-6H-purin-6-one 
• 91382-84-2 (+/-)-4α-adenin-9-yl-2α,3β-dihydroxy-1α-cyclopentanemethanol 

Relevant academic research and scientific papers

Synthesis of 4a-Carba-d-lyxofuranose Derivatives and Their Evaluation as Inhibitors of GH38 α-Mannosidases

A synthetic approach to 4a-carba-d-lyxofuranose derivatives starting from d-lyxose is described. The protected 4a-carba-β-d-lyxofuranose was employed as the key intermediate for the synthesis of 4a-carba-d-lyxofuranose derivatives including novel 1-amino-1-deoxy-4a-carba-d-lyxofuranoses. Synthesized 4a-carba-d-lyxofuranoses were evaluated as inhibitors of GH38 α-mannosidases, namely, the Golgi (GMIIb) and lysosomal (LManII) α-mannosidases from Drosophila melanogaster and commercial Jack bean α-mannosidase (JBMan) from Canavalia ensiformis. The biochemical evaluation revealed that only 1-amino-1-deoxy-4a-carba-β-d-lyxofuranose exhibited reasonable inhibitory activity against GMIIb (IC50 = 200 μm). In addition, the results of biological evaluation were discussed by means of molecular modelling.

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.