189151-77-7

Upstream product

• 108549-23-1 Dibenzyl N,N-diisopropylphosphoramidite 
• 189151-66-4 methyl 2',5,6'-tri-O-benzyl-3-O-α-D-glucopyranosyl-β-D-ribofuranoside 
• 100-39-0 benzyl bromide 
• 7473-45-2 1-O-methyl-D-ribofuranose 
• 189151-18-6 methyl 5-O-benzyl-2-O-p-methoxybenzyl-β-D-ribofuranoside 
• 189151-29-9 methyl 5-O-benzyl-2,3-O-p-methoxybenzylidene-β-D-ribofuranoside 
• 33981-58-7 methyl 2,3-O-p-methoxybenzylidene-β-D-ribofuranoside 

Relevant academic research and scientific papers

Synthesis of glucopyranoside-based ligands for D-myo-inositol 1,4,5-trisphosphate receptors

Adenophostins A and B are naturally occurring glyconucleotides that interact potently with receptors for D-myo-inositol 1,4,5-trisphosphate, an important second messenger molecule in most cell types. Here we describe the design and synthesis of glucopyranoside-based analogues of adenophostin A lacking the adenine component. The key synthetic strategy involves glycosylation of selectively protected alcohols, derived from methyl β-D-ribofuranoside or 1,4-anhydroerythritol, using glycosyl donors synthesised from 2,6-di-O-benzyl-D-glucopyranose derivatives. Further elaboration and deprotection of the coupled products gave two trisphosphate analogues; methyl 3-O-α-D-glucopyranosyl-β-D-ribofuranoside 2,3′,4′-trisphosphate ("ribophostin") and (3′S,4′R)-3′-hydroxytetrahydrofuran-4′-yl α-D-glucopyranoside 3,4,3′-trisphosphosphate ("furanophostin"). The route to furanophostin was further modified to give (3′S,4′R)-3′-hydroxytetrahydrofuran-4′-yl α-D-glucopyranoside 3′-phosphate 3,4-bisphosphorothioate, the first phosphorothioate-containing adenophostin analogue.

A disaccharide polyphosphate mimic of 1D-myo-inositol 1,4,5-trisphosphate

A concise route from D-glucose and D-ribose to a potent sugar polyphosphate second messenger mimic related to adenophostin A is described; a role for the adenine base of the adenophostins is suggested.