77870-70-3

Upstream product

• 77870-67-8 N-((2S,3R,4R,5S,6R)-4-Benzyloxy-5-fluoro-2-methoxy-6-trityloxymethyl-tetrahydro-pyran-3-yl)-benzamide 
• 77870-42-9 methyl 2-benzamido-3-O-benzyl-2-deoxy-4,6-di-O-mesyl-α-D-glucopyranoside 
• 77870-60-1 methyl 2-benzamido-3-O-benzyl-2-deoxy-α-D-galactopyranoside 
• 77870-41-8 methyl 2-benzamido-3-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 4288-73-7 methyl 2-benzamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 77870-71-4 methyl 2-benzamido-2,4-dideoxy-4-fluoro-α-D-glucopyranoside 
• 77870-66-7 methyl 2-benzamido-3-O-benzyl-2-deoxy-4-O-mesyl-6-O-trityl-α-D-galactopyranoside 
• 77870-40-7 methyl 2-benzamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 77870-68-9 methyl 2-benzamido-3-O-benzyl-2,4-dideoxy-4-fluoro-α-D-glucopyranoside 
• 290819-64-6 methyl 2-acetamido-3,6-di-O-benzoyl-2,4-dideoxy-4-fluoro-α-D-glucopyranoside 
• 6082-04-8 methyl 2-acetylamido-2-deoxy-D-glucoside 
• 269065-36-3 methyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-α-D-glucopyranoside 
• 176691-03-5 methyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-4-O-trifluoromethanesulfonyl-β-D-galactopyranoside 
• 176691-02-4 methyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-α-D-galactopyranoside 

Relevant academic research and scientific papers

Synthesis of 4-deoxy-4-fluoro analogues of 2-acetamido-2-deoxy-D-glucose and 2-acetamido-2-deoxy-D-galactose and their effects on cellular glycosaminoglycan biosynthesis

4-Deoxy-4-fluoro analogues of 2-acetamido-2-deoxy-D-glucose and 2-acetamido-2-deoxy-D-galactose were synthesized and evaluated as inhibitors of hepatic glycosaminoglycan biosynthesis. 2-Acetamido-1,3,6-tri-O-acetyl-2,4-dideoxy-4-fluoro-D-glucopyranose (16) exhibited a reduction of [3H]GlcN and [35S]SO4 incorporation into hepatocyte cellular glycosaminoglycans to 12 and 18%, respectively, of the control cells, at 1.0 mM. Similarly, 2-acetamido-1,3,6-tri-O-acetyl-2,4-dideoxy-4-fluoro-D-galactopyranose (31) exhibited a reduction of [3H]GlcN and [35S]SO4 incorporation to 1 and 9%, respectively, of the control cells, at 1.0 mM. Unlike 16, 31 exhibited a reduction of [14C]Leu incorporation into cellular protein to 57% of control cells, at 1.0 mM. Copyright (C) 2000 Elsevier Science Ltd.

Synthesis of fluoro derivatives of 2-amino-2-deoxy-D-galactose and D-glucose

Selective fluoride displacement of the 6-mesyloxy group of methyl 2-benzamido-3-O-benzyl-2-deoxy-4,6-di-O-mesyl-α-D-glucopyranoside 4 gave the 6-fluoride 5.Subsequent removal of the blocking substituents afforded 2-amino-2,6-dideoxy-6-fluoro-D-glucose, is