211630-37-4

Upstream product

• 106-95-6 allyl bromide 
• 211630-36-3 (S)-1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-trityloxy-ethanol 
• 114184-97-3 (S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-1,2-diol 
• 114184-94-0 ethyl (R)-2-[(4'R)-2',2'-dimethyl-1,3-dioxolan-4'-yl]-2-hydroxyacetate 

Downstream Products

• 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 

Relevant academic research and scientific papers

Synthesis of 1-O-[(3S,4R)-3-hydroxytetrahydrofuran-4-yl]-α-D- glucopyranoside 3,4,3'-triphosphate as a novel potent IP3 receptor ligand

1-O-[(3S,4R)-3-Hydroxytetrahydrofuran-4-yl]-α-D-glucopyranoside 3,4,3'- triphosphate (5) was designed and synthesized as a novel IP3 receptor ligand. This compound bound strongly to IP3 receptor from porcine cerebella with an affinity comparable to that of IP3.

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.