158227-76-0

Upstream product

• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 158227-77-1 1-Amino-5-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-1H-pyrrole-2-carbaldehyde 
• 158227-78-2 1-Amino-5-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-1H-pyrrole-2-carbonitrile 
• 158227-80-6 7-((2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-tetrahydrofuran-2-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine 

Relevant academic research and scientific papers

4-Aza-7,9-dideazaadenosine, a new cytotoxic synthetic C-nucleoside analogue of adenosine

The first synthesis of 10, the pyrrolo[2,1-f][1,2,4]triazine C-nucleoside congener of adenosine is described. The key intermediate ribofuranosyl pyrrole 4 is obtained by the direct C-ribosylation of pyrrolemagnesiumbromide with 2,3,5-tri-O-benzyl ribose followed by an acid-catalyzed dehydration. Vilsmeier formylation of 4 followed by N-amination and CHO -> CN conversion affords N-amino nitrile intermediate 7 which can be cyclized with formamidine acetate to the blocked title compound 9. Hydrogenolytic debenzylation completes the synthesis. In vitro growth inhibitory activities of 10 against leukemic cell lines (0.8 - 15 nM) are comparable to those of 9- deazaadenosine.