188540-60-5

Upstream product

• 7028-48-0 Phenylacetaldehyde oxime 
• 188540-59-2 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-1-thio-β-D-glucopyranose 
• 34245-85-7 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-glucopyranosyl bromide 
• 188540-57-0 Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-fluoro-6-tritylsulfanyl-tetrahydro-pyran-4-yl ester 
• 188540-58-1 3,4,6-tri-O-acetyl-1-S-acetyl-2-deoxy-2-fluoro-1-thio-β-D-glucopyranose 

Relevant academic research and scientific papers

Synthesis of 2-deoxy-2-fluoro-glucotropaeolin, a thioglucosidase inhibitor

S(N)2-Displacement of the anomeric bromine atom in 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-glucopyranosyl bromide with the tetrabutylammonium salt of triphenylmethanethiol afforded the corresponding trityl 1-thio-β-D-glucoside which led to the fully protected S-acetyl-2-fluoro-1-thio-β-D-grucose derivative, and then to the free thiol 5 by selective S-deacetylation at low temperature. 2-Fluoro-glucotropaeolin (1) was obtained by a conventional procedure from 5.