133329-69-8

Upstream product

• 119138-92-0 6-Amino-9-methyl-7H-purin-8(9H)-one 
• 133329-66-5 1-Benzyl-6-imino-9-methyl-1,6,7,9-tetrahydro-purin-8-one 
• 133329-67-6 7,9-dihydro-9-methyl-6-<(phenylmethyl)amino>-8H-purin-8-one 
• 74-88-4 methyl iodide 

Downstream Products

• 133329-70-1 1,6,7,9-tetrahydro-1,9-dimethyl-6-<(phenylmethyl)imino>-8H-purin-8-one hydrochloride 
• 98601-03-7 6-imino-1,9-dimethyl-8-oxopurine 

Relevant academic research and scientific papers

Purines. LVII. Regioselective alkylation of N6,9-disubstituted 8- oxoadenines: Syntheses of the sea anemone purine caissarone and some positional isomers and analogues

The first total synthesis of caissarone hydrochloride (1), a constituent of the sea anemone Bunodosoma caissarum, has been accomplished via a two- step route starting from N6,9-dimethyl-8-oxoadenine (3), which is obtainable from 9-methyladenine (5) through a four-step route. The key step in the synthesis is the regioselective methylation of 3 at N(3), which has been designed on the basis of a methylation study of N6-benzyl-9-methyl-8- oxoadenine (11). Some positional isomers (19, 24, and 31) and analogues (8, 26, and 32) of 1 have also been synthesized. A 1H-NMR spectroscopic study has suggested that the free base (23) of caissarone is capable of forming a hetero-base pair (such as 41) with 2',3',5'-tri-O-acetylguanosine (40) in Me2SO-d6.

SYNTHESIS OF THE SEA ANEMONE PURINE CAISSARONE

On the basis of a methylation of N6-benzyl-9-methyl-8-oxoadenine (8), the first synthesis of caissarone hydrochloride (1) has been achieved via a two-step route including methylation of N6-methyl analogue (3).