211630-26-1

Upstream product

• 211630-34-1 1,6-di-O-acetyl-3,4-di-O-allyl-2-O-benzyl-D-glucopyranose 

Downstream Products

• 219530-55-9 (2R,3R,4S,5R,6S)-3,4-Bis-allyloxy-6-((3S,4R,5R)-4-allyloxy-5-benzyloxymethyl-tetrahydro-furan-3-yloxy)-5-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran 
• 219530-58-2 Phosphoric acid dibenzyl ester (2R,3R,4R,5R,6S)-5-benzyloxy-2-benzyloxymethyl-6-[(3S,4R,5R)-5-benzyloxymethyl-4-(bis-benzyloxy-phosphoryloxy)-tetrahydro-furan-3-yloxy]-4-(bis-benzyloxy-phosphoryloxy)-tetrahydro-pyran-3-yl ester 
• 219530-53-7 (3'S,4'R)-3'-dibenzyloxyphosphoryloxytetrahydrofuran-4'-yl 2,6-di-O-benzyl-3,4-bis-O-(dibenzyloxyphosphoryl)-α-D-glucopyranoside 
• 221356-66-7 (3'S,4'R)-3'-hydroxytetrahydrofuran-4'-yl 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 

Relevant academic research and scientific papers

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.

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.