304891-24-5

Upstream product

• 96192-07-3 2,3,5-tri-O-benzyl-L-arabinofuranose 
• 129378-52-5 2-tert-butyldimethylsilyl-N,N-dimethylimidazole-1-sulfonamide 
• 16838-89-4 2,3,5-tri-O-benzyl-D-xylofuranose 
• 222419-00-3 lithium salt of 2-tert-butyldimethylsilyl-N,N-dimethylimidazole-1-sulfonamide 

Downstream Products

• 391249-76-6 4(5)-(2,3,5-tri-O-benzyl-α-D-xylofuranosyl)imidazole 
• 304891-25-6 (11R)-4-(2',3',5'-tri-O-benzyl-L-arabinosyl)imidazole 

Relevant academic research and scientific papers

Synthesis of 4(5)-(α-D-Xylofuranosyl)imidazole starting from L-arabinose: Mitsunobu cyclization via C4′-oxyphosphonium intermediate

4(5)-(α-D-Xylofuranosyl)imidazole (3) was synthesized using Mitsunobu cyclization via C4′-oxyphosphonium intermediate (5) starting from L-arabinose.

Synthesis of 4(5)-(5'-amino-5'-deoxy-α-L-arabino-furanosyl)imidazole and its 5'-derivatives using modified Mitsunobu cyclization: Synthetic studies toward novel histamine H3-ligands

The modified Mitsunobu cyclization of 4-(2',3',5'-tri-O-benzyl-L-arabinosyl)imidazole (11RS) using N,N,N',N'-tetramethylazodicarboxamide and Bu3P followed by ethoxycarbonylation produced a mixture (α / β = 20 / 1) of ethyl 4-(2',3',5'-tri-O-benzyl-L-arabinofuranosyl)-imidazole-1-carboxylate (13). The compound (13) was converted into ethyl 4-(5'-deoxy-5'-phthaloylamino-L-arabinofuranosyl)imidazole-1-carboxylate (15), which was subsequently led to 4-(5'-amino-5'-deoxy-α-L-arabinofuranosyl)imidazole (2α). The 4(5)-{5-[N-(4-chlorophenyl)thio-ureido]-α-L-arabinofuranosyl}imidazole (18), 4(5)-{5-[N-(4-chlorophenyl)-ureido]-α-L-arabinofuranosyl}imidazole (19), and 1-cyano-2-methyl-3-{5-deoxy-1-[1H-imidazol-4(5)-yl]-α-L-arabinofuranosyl}g uanidine (20) were efficiently synthesized from 2α.