368451-98-3

Upstream product

• 340969-76-8 3,4-di-O-benzyl-1,2-O-isopropylidene-β-D-fructopyranose 
• 99648-59-6 3,4-di-O-benzoyl-1,2-O-isopropylidene-β-D-fructopyranose 
• 99648-49-4 3-O-benzoyl-1,2-O-isopropylidene-β-D-fructopyranose 
• 100-39-0 benzyl bromide 
• 368451-88-1 3,4-di-O-benzyl-1,2-O-isopropylidene-5-O-p-nitrobenzoyl-β-L-sorbopyranose 

Relevant academic research and scientific papers

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.