303014-75-7

Upstream product

• 204771-46-0 (S)-8-Bromo-9-[2-hydroxy-3-(trityloxy)propyl]adenine 
• 66224-66-6 adenine 
• 129940-50-7 (S)-tritylglycidol 
• 6974-78-3 8-bromoadenine 
• 7390-62-7 6-amino-7,9-dihydro-8H-purine-8-thione 
• 2508-06-7 8-(methylsulfanyl)-9H-purin-6-amine 

Relevant academic research and scientific papers

Synthesis of acyclic nucleoside and nucleotide analogs derived from 6-amino-7H-purine-8(9H)-thione and 8-(methylsulfanyl)adenine

Reaction of 8-bromoadenine derivatives 1 with thiourea in ethanol or butanol was used for the synthesis of the corresponding N9-substituted 6-amino-7H-purine-8(9H)-thiones 2. 8-(Methylsulfanyl)adenine derivatives 3 were prepared by reaction of thiones 2 with iodomethane in 1 M sodium methoxide or in aqueous 1.5 M potassium hydroxide. Alkylation of 6-amino-7H-purine-8(9H)-thione (2a) proceeds preferentially on the sulfur atom. Under similar conditions, alkylation of 8-(methylsulfanyl)adenine (3a) with diverse alkylation agents afforded N9-substituted adenine derivatives 3 and 6, and N3-substituted adenine derivatives 5 and 7. 8,3′-S-Anhydro derivatives 9 were prepared in good yields by cyclization of 6-amino-7H-purine-8(9H)-thiones 2d and 2f under the Mitsunobu reaction conditions.

Synthesis of acyclic nucleoside and nucleotide analogs derived from 6-amino-7H-purin-8(9H)-one

Reaction of 8-bromoadenine derivatives 2 with sodium acetate in acetic acid and cleavage of (S)-7-[(trityloxy)methyl]-7,8-dihydro[1,3]oxazolo[3,2-e]purin-4-amine (12) and diisopropyl (S)-[[(4-amino-8,9-dihydro-7H-[1,3]oxazino[3,2-e]purin-8-yl)oxy]methyl]phosphona te (13a) were used for the synthesis of the corresponding N9-substituted derivatives of 6-amino-7H-purin-8(9H)-one 3a-3c and 7. Alkylation of 6-amino-7H-purin-8(9H)-one (3a) with diverse alkylation agents afforded the title N9-monosubstituted 3b, 3d and 7a and N7,N9-disubstituted acyclic nucleoside and nucleotide analogs 6b, 6d and 8a.