482359-41-1

Upstream product

• 4330-34-1 methyl 3,5-di-O-toluoyl-2-deoxy-D-ribofuranose 
• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 
• 482359-34-2 1-(2'-deoxy-3',5'-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-5-nitroimidazole 

Downstream Products

• 482359-42-2 5-amino-4-(2,2-dicyanovinyl)-1-(2'-deoxy-3',5'-di-O-p-toluoyl-β-D-ribofuranosyl)imidazole 

Relevant academic research and scientific papers

Preparation of 9-substituted pyridine-stretched adenines and hypoxanthines

9-Methylsulfanyl pyridine-stretched adenine and hypoxanthine derivatives have been prepared via regioselective reaction of a 5-aminoimidazole with 2-(bis-methylsulfanylmethylene)malononitrile [(NC)2C=C(SMe) 2]. The 9-methylsulfanyl substituent can be replaced by sequential oxidation and substitution by nucleophiles including amines. Georg Thieme Verlag Stuttgart.

Preparation of pyridine-stretched 2′-deoxyhypoxanthosine phosphoramidite

Pyridine-stretched 2-deoxyhypoxanthosine (strH) phosphoramidite was prepared in eight steps from Hoffer's sugar (2-deoxy-3,5-di-O-(p-toluoyl)-a-D-erythro-pentofuranosyl chloride). Improved synthesis of the Hoffer sugar was achieved without need for distillation or chromatographic separation of intermediates, or use of gaseous HCl. Conditions were optimised to provide a key nitrile intermediate for the preparation of strH whereby the cesium salt of 4(5)-nitroimidazole was glycosylated using Hoffer's sugar. The nitrile intermediate was also used to prepare pyridine-stretched 2-deoxyadenosine (strA) and pyridine-stretched 2-deoxy-2,6-diaminonebulamine (strD). Preliminary studies indicate that strH forms a stronger, size-expanded base pair with adenine compared with the Watson-Crick thymine-adenine base pair.

Synthesis of pyridine-stretched 2′-deoxynucleosides

Synthesis of novel pyridine-stretched nucleoside (PSN) analogues of adenine (strA) (1), 2,6-diaminopurine (strD) (15) and hypoxanthine (strH) (17) from 4(5)-nitroimidazole has been achieved. Glycosylation of 4(5)-nitroimidazole was optimized to give consi