90358-18-2

Upstream product

• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 
• 90358-17-1 2-Amino-4-methoxy-5-methyl-7H-pyrrolo<2,3-d>pyrimidin 
• 90358-16-0 4-Chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamine 
• 65062-57-9 2-Amino-5-methyl-3H-pyrrolo<2,3-d>pyrimidin-4(7H)-on 

Relevant academic research and scientific papers

Synthesis and Furanoside/Pyranoside Isomerization of 7-Deaza-2'-deoxy-7-methylguanosine

7-Deaza-2'-deoxy-methylguanosine (2), an isoster of the zwitterionic 2'-deoxy-7-methylguanosine (1) and its α anomer 10b was synthesized.Phase-transfer glycosylation of 2-amino-4-methoxy-5-methyl-7H-pyrrolopyrimidine (6b) with 1-chloro-2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranose (7a) caused regioselective glycosylation of position 7 to give the anomers 8 and 9 in 87percent yield.Deprotection of the sugar moiety by sodium methanolate gave the nucleosides 10a and 11; subsequent cleavage of the 4-methoxy group by aluminium chloride in DMF leads to 2 and its α anomer 10b.Treatment of 10a with 7 N HCl/dioxane resulted in isomerization and demethylation forming the furanosides 10b and 2 and the pyranosides 12b and 13b.Isomerization of 10a without demethylation was achieved with 1 N hydrochloric acid and gave the furanosides 10a and 11 as well as the pyranosides 12a and 13a.