3317-09-7

Upstream product

• 100428-14-6 methyl 2-benzoylamino-O⁴,O⁶-(R)-benzylidene-O³-methanesulfonyl-α-D-2-deoxy-altropyranoside 
• 84278-01-3 methyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-α-D-altropyranoside 
• 6038-60-4 methyl 2-amino-4,6-O-benzylidene-2-deoxy-α-D-altropyranoside 
• 149033-49-8 methyl 4,6-O-benzylidene-2-deoxy-3-O-mesyl-2-phthalimido-α-D-altropyranoside 

Downstream Products

• 28225-01-6 (4aR)-6c-methoxy-8-(4-nitro-phenyl)-2c-phenyl-(4ar,6ac,9ac,9bt)-4,4a,6,6a,9a,9b-hexahydro-[1,3]dioxino[4',5':5,6]pyrano[3,4-d]oxazole 
• 28225-02-7 (4aR)-6c-methoxy-8-(4-methoxy-phenyl)-2c-phenyl-(4ar,6ac,9ac,9bt)-4,4a,6,6a,9a,9b-hexahydro-[1,3]dioxino[4',5':5,6]pyrano[3,4-d]oxazole 
• 3396-88-1 methyl O⁴,O⁶-(R)-benzylidene-2,3-(2,4-dinitro-phenylazanediyl)-α-D-2,3-dideoxy-mannopyranoside 
• 3150-18-3 methyl 2,3-acetylazanediyl-O⁴,O⁶-(R)-benzylidene-α-D-2,3-dideoxy-mannopyranoside 

Relevant academic research and scientific papers

Fluorinated carbohydrates as potential plasma membrane modifiers. Synthesis of 3-deoxy-3-fluoro derivatives of 2-acetamido-2-deoxy-D-hexopyranoses

Treatment of benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-allopyranoside with diethylaminosulfur trifluoride or of the 3-O-mesyl derivative with tetrabutylammonium fluoride gave the 2,3-unsaturated compound instead of the expected 3-deoxy-3-fluoro derivative.The latter was obtained when benzyl 2-acetamido-4,6-di-O-benzyl-2-deoxy-3-O-mesyl-α-D-allopyranoside was treated with potassium fluoride.Methyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-altropyranoside was converted into the 2-acetamido- and 2-phthalimido-3-O-mesyl derivatives; when treated with fluoride nucleophile, these gave only the 2,3-aziridine derivative.However, treatment of the 2-azido-2-deoxy derivative with diethylaminosulfur trifluoride gave methyl 2-azido-2,3-dideoxy-3-fluoro-α-D-mannopyranoside which, after reduction, deprotection, and acetylation, gave the acetylated derivative of methyl 2-acetamido-2,3-dideoxy-3-fluoro-α-D-mannopyranoside in excellent yield.These acetylated 3-fluoro derivatives exhibited inhibition of cell growth of murine L1210 leukemia cells in culture at micromolar concentrations.