244612-06-4

Upstream product

• 244612-04-2 allyl 4,6-O-benzylidene-2,3-bis-O-(methanesulfonyl)-α-D-glucopyranoside 
• 93382-48-0 allyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 244612-05-3 allyl 2-O-benzyl-4,6-O-benzylidene-α-D-altropyranoside 

Downstream Products

• 244612-13-3 allyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-altropyranoside 
• 244612-12-2 allyl 2,3,4-tri-O-benzyl-6-O-[(4-methylphenyl)sulfonyl]-α-D-altropyranoside 
• 244612-17-7 (Z)-2,3,4-tri-O-benzyl-6-deoxy-D-altrose O-[(tert-butyl)diphenylsilyl]oxime 
• 244612-16-6 (E)-2,3,4-tri-O-benzyl-6-deoxy-D-altrose O-[(tert-butyl)diphenylsilyl]oxime 
• 244612-18-8 (E)-2,3,4-tri-O-benzyl-6-deoxy-5-O-[(4-methylphenyl)sulfonyl]-D-altrose O-[(tert-butyl)diphenylsilyl]oxime 
• 244612-11-1 allyl 2,3,4-tri-O-benzyl-α-D-altropyranoside 

Relevant academic research and scientific papers

Synthesis of an L-fucose-derived cyclic nitrone and its conversion to α-L-fucosidase inhibitors

The L-fuco-nitrone 1 has been synthesized from allyl 4,6-O-benzylidene- α-D-glucopyranoside (4) in 11 steps and an overall yield of 18%. The key step is the intramolecular alkylation of an intermediary 1,1- bis(hydroxylamine) derived from the tosyloxy oximes (E/Z)-2. The nitrone 1 has been transformed into the diamine 30, the indolizidines 39 and 40, the indolizidinones 34 and 35, and the imidazole 44, all inhibiting bovine epididymis α-L-fucosidase with IC50 values between 105 nM and 240 μM.