368452-06-6

Upstream product

• 100-39-0 benzyl bromide 
• 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 
• 340969-76-8 3,4-di-O-benzyl-1,2-O-isopropylidene-β-D-fructopyranose 

Downstream Products

• 368452-24-8 5-azideo-3,4-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-L-sorbopyranose 
• 476156-42-0 (2R,3R,4R,5R)-3,4-dibenzyloxy-N-tert-butyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine 
• 487040-51-7 5-azido-3,4-di-O-benzyl-1-O-tert-butyldiphenylsilyl-5-deoxy-β-D-fructopyranose 
• 487040-55-1 (2R,3R,4R,5R)-3,4-dibenzyloxy-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine 
• 487040-50-6 5-azido-3,4-di-O-benzyl-5-deoxy-β-D-fructopyranose 

Relevant academic research and scientific papers

Polyhydroxylated pyrrolidines. Part 2: Highly stereoselective synthesis of partially protected DMDP derivatives from D-fructose

The readily available 3,4-di-O-benzyl-1,2-O-isopropylidene-β-D-fructopyranose 2 was straightforwardly transformed into 5-azido-3,4-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-D-fructopyranose 4, after treatment under modified Garegg's conditions followed by reaction of the resulting 3,4-di-O-benzyl-5-deoxy-5-iodo-1,2-O-isopropylidene-α-L-sorbopyranose 3 with sodium azide in DMF. Cleavage of the acetonide of 4 to afford 6 followed by regioselective O-tert-butyldiphenylsilylation at C(1)OH afforded 7. Hydrogenation of 7 proceeded with high stereoselectivity yielding 3,4-di-O-benzyl-1-O-tert-butyldiphenylsilyl-2,5-dideoxy-2,5-imino-D-mannitol 1, confirmed by its O-desilylation to 8. Compound 1 was subjected to different N-protection reactions to afford the corresponding N-allyl (1a), N-benzyl (1b), and N-tert-butyloxycarbonyl (1c) derivatives.

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.