75829-33-3

Upstream product

• 13190-81-3 N-((1S,3R,4S)-2,3-Dihydroxy-4-hydroxymethyl-cyclopentyl)-acetamide 
• 61865-49-4 ester methylique de l'acide (acetamido-cis-4)-cyclopentene-2-carboxylique 
• 126958-90-5 (1R,3S,4S)-4-Acetylamino-2,3-dihydroxy-cyclopentanecarboxylic acid methyl ester 
• 13190-81-3 N-((1R,3S,4R)-2,3-Dihydroxy-4-hydroxymethyl-cyclopentyl)-acetamide 
• 126958-90-5 (1S,3R,4R)-4-Acetylamino-2,3-dihydroxy-cyclopentanecarboxylic acid methyl ester 
• 61865-51-8 (1α,2α,3α,4α)-4-acetamido-2,3-epoxycyclopentylmethyl acetate 
• 162427-15-8 3-oxo-2-aza-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid tert-butyl ester 
• 62413-48-3 (+/-)-(1α,2β,3α,4α)-4-acetamido-2,3-diacetoxy-1-cyclopentanemethyl acetate 
• 127061-46-5 methyl (+)-cis-4-acetamidocyclopent-2-enecarboxylate 
• 112531-51-8 (-)-(1S,4R)-4-(acetylamino)-2-cyclopentene-1-carboxylic acid 
• 69919-17-1 methyl (+)-(1R,4S)-4-acetamido-cyclopent-2-ene carboxylate 

Downstream Products

• 75797-17-0 (+/-)-2-amino-6-chloro-9-<2α,3β-dihydroxy-4α-(hydroxymethyl)cyclopent-1α-yl>purine 
• 50619-39-1 (+/-)-2,5-diamino-4-N-<2α,3β-dihydroxy-4α-(hydroxymethyl)cyclopent-1α-yl>amino-6-chloropyrimidine 

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.

2-azabicyclo[2.2.1]hept-5-en-3-one epoxide: A versatile intermediate for the synthesis of cyclopentyl carbocyclic 2-deoxy-, 3-deoxy- and ara- ribonucleoside analogues.

5,6-Epoxy-exo-2-azabicyclo[2.2.1]heptan-3-one has been used as a versatile intermediate in the synthesis of 2-deoxy-, 3-deoxy- and ara- cyclopentyl carbocyclic nucleosides. An efficient, short synthesis of the (+) carbocyclic thymidine 13 is reported.

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.