219530-53-7

Upstream product

• 211630-41-0 (3S,4R)-3-acetoxytetrahydrofuran-4-yl 3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranoside 
• 211630-40-9 (2R,3R,4S,5R,6S)-3,4-Bis-allyloxy-6-((3R,4S)-4-allyloxy-tetrahydro-furan-3-yloxy)-5-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran 
• 211630-34-1 1,6-di-O-acetyl-3,4-di-O-allyl-2-O-benzyl-D-glucopyranose 
• 211630-26-1 6-O-acetyl-3,4-di-O-allyl-2-O-benzyl-D-glucopyranosyl fluoride 
• 221356-66-7 (3'S,4'R)-3'-hydroxytetrahydrofuran-4'-yl 2,6-di-O-benzyl-α-D-glucopyranoside 
• 108549-23-1 Dibenzyl N,N-diisopropylphosphoramidite 
• 221356-65-6 (3'S,4'R)-3'-(p-methoxybenzyloxy)tetrahydrofuran-4'-yl 2,6-di-O-benzyl-3,4-di-O-p-methoxybenzyl-α-D-glucopyranoside 
• 221356-64-5 2,6-di-O-benzyl-3,4-di-O-p-methoxybenzyl-D-glucopyranosyl dimethyl phosphite 

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.

Simplification of adenophostin a defines a minimal structure for potent glucopyranoside-based mimics of D-myo-inositol 1,4,5-trisphosphate

The synthesis of 1-O-[(3S,4R)-3-hydroxytetrahydrofuran-4-yl]-α-D- glucopyranoside 3,4,3'trisphosphate (7), a novel Ca2+ mobilising agonist at the Ins(1,4,5)P3 receptor, designed by excision of two motifs of adenophostin A is reported, defining a potential minimal structure for potent glucopyranoside-based agonists of Ins(1,4,5)P3 receptors.

Synthesis of adenophostin analogues lacking the adenine moiety as novel potent IP3 receptor ligands: Some structural requirements for the significant activity of adenophostin a

1-O-Tetrahydrofuranyl-α-D-glucopyranose derivatives 5-8 were designed and synthesized as novel IP3 receptor ligands. The glycosidation reactions between fluoroglycosyl donor 23 and tetrahydrofuran derivatives 11-14 as glycosyl acceptors selectively gave the corresponding α-glycosides, which were converted into the target compounds 5-8 via the introduction of phosphate groups using the phosphoramidite method. Among these compounds, 1- O-tetrahydrofuranyl-α-D-glucopyranose trisphosphate derivatives 5 and 8 significantly inhibited the binding of [3H] IP3 to IP3 receptor from porcine cerebella, with IC50 values of 25 and 27 nM, respectively, which were comparable to the affinity of IP3 itself.