368452-03-3

Upstream product

• 98-88-4 benzoyl chloride 
• 76573-34-7 (-)-3-deoxy-1,2:4,5-di-O-isopropylidene-β-D-fructofuranos-3-yl benzoate 
• 99648-49-4 3-O-benzoyl-1,2-O-isopropylidene-β-D-fructopyranose 
• 25018-67-1 1,2;4,5-di-O-isopropylidene-β-D-(-)-fructopyranose 
• 99648-59-6 3,4-di-O-benzoyl-1,2-O-isopropylidene-β-D-fructopyranose 

Downstream Products

• 368452-27-1 5-S-acetyl-3,4-di-O-benzoyl-1,2-O-acetyl-5-thio-α-D-fructopyranose 
• 697288-29-2 (2R,3R,4R,5R)-3,4-Dihydroxy-2,5-bis-hydroxymethyl-pyrrolidine-1-carbothioic acid phenylamide 
• 94801-02-2 5-azido-5-deoxy-D-fructopyranose 
• 59920-31-9 2,5-dideoxy-2,5-imino-D-mannitol 
• 368452-17-9 5-S-acetyl-3,4-di-O-benzoyl-1,2-O-isopropylidene-5-thio-β-D-fructopyranose 
• 368452-21-5 5-azideo-3,4-di-O-benzoyl-5-deoxy-1,2-O-isopropylidene-β-L-sorbopyranose 

Relevant academic research and scientific papers

Pseudoamide-Type Pyrrolidine and Pyrrolizidine Glycomimetics and Their Inhibitory Activities against Glycosidases

Coupling reaction of (2R,3R,4R,5R)-2,5-hydroxy-methyl-3,4-dihydroxypyrrolidine (DMDP) with isothiocyanates afforded the corresponding thiourea adducts, which were transformed into isourea-type bicyclic oxapyrrolizidine glycomimetics by mercury(II) oxide-assisted intramolecular sulfur displacement. Cyclic carbamate and thiocarbamate analogues were also prepared by direct carbonylation or thiocarbonylation of DMDP. Evaluation of the glycosidase inhibitory properties demonstrated that remarkable specificities in enzyme inhibition can be achieved upon modifications on the pseudoaglyconic side chain and on the nature of the sp2-hybridized endocyclic ring nitrogen.

D-Fructose-L-sorbose interconversions. Access to 5-thio-D-fructose and interaction with the D-fructose transporter, GLUT5

Epimerisation and subsequent functionalization at C-5 of D-fructopyranose derivatives under Mitsunobu and Garegg's conditions provided efficient access to 5-thio-D-fructose (2) as well as to 5-azido-5-deoxy-1,2-O-isopropylidene-β-D-fructopyranose (19), a known precursor to 2,5-deoxy-2,5-imino-D-mannitol (3). The interaction of 2 with the D-fructose transporter GLUT5, was found to be weaker than that of D-fructose, a result that suggests involvement of the ring oxygen atom in the recognition of D-fructose by GLUT5.