210825-01-7

Upstream product

• 100-39-0 benzyl bromide 
• 2973-77-5 3,5-dibromo-4-hydroxybenzaldehyde 
• 31077-24-4 8-oxo-7,8-dihydro-2'-deoxyguanosine 
• 249515-06-8 4-(benzyloxy)-3,5-dibromobenzaldehyde 
• 210825-00-6 N-(4-benzyloxy-3,5-dibromobenzyl)-2'-deoxy-8-oxoadenosine 
• 249515-07-9 4-benzyloxy-3,5-dibromobenzyl alcohol 
• 210825-04-0 1-(4-Benzyloxy-3,5-dibromo-benzyl)-9-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-imino-1,6,7,9-tetrahydro-purin-8-one 
• 1026812-13-4 4-benzyloxy-3,5-dibromobenzyl bromide 
• 123-08-0 4-hydroxy-benzaldehyde 

Relevant academic research and scientific papers

Syntheses of the marine ascidian purine aplidiamine and its 9-β-D- ribofuranoside

The title nucleoside 9 was synthesized by alkylation of 8-oxoadenosine (7) with 4-benzyloxy-3,5-dibromobenzyl bromide, followed by Dimroth rearrangement and acid hydrolysis. 2'-Deoxy version of this reaction sequence accomplished the first synthesis of aplidiamine (6).

Synthesis and structure of the marine ascidian 8-oxoadenine aplidiamine

Alkylation of 8-oxoadenosine (13) with 4-benzyloxy-3,5-dibromobenzyl bromide (20), followed by Dimroth rearrangement and acid hydrolysis, provided N-(3,5-dibromo-4-hydroxybenzyl)-8-oxoadenosine (15). The 2'- deoxy version of this reaction sequence accomplished the first synthesis of N-(3,5-dibromo-4- hydroxybenzyl)-8-oxoadenine (16), which is the correct expression for marine ascidian purine aplidiamine.