- Synthesis and oxidation of thioglicosides underlain by neomenthanethiol, D-glucose, and D-fructose
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Synthesis of sulfides proceeding from neomenthanethiol, 1,2-O-isopropylidene-α-D-glucofuranose and 2,3:4,5-di-O-isopropylidene- β-D-fructopyranose was performed to get 65 and 54% yield respectively. Oxidation of the sulfides afforded diastereomeric sulfoxides in the yields from 40 to 53%, and diastereomeric excess (de) up to 36%. After removing the isopropylidene protection from 1-deoxy-1-[(1S,2S,5R)-2-isopropyl-5- methylcyclohexylsulfanyl]-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose a water-soluble sulfide was obtained.
- Pestova,Izmest'Ev,Rubtsova,Kuchin
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p. 670 - 677
(2014/07/08)
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- Synthesis of [18F]-6-deoxy-6-fluoro-D-glucose ([ 18F]6FDG), a potential tracer of glucose transport
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With the goal of developing a PET radioligand for the in vivo assessment of glucose transport, 6-deoxy-6-[18F]fluoro-D-glucose ([ 18F]6FDG) was prepared in two steps from 18F-. Starting with D-glucose, the tosyl- and mesyl-derivatives of 3,5-O-benzylidene-1,2-O-isopropylidene-α-D-glucofuranose were prepared by known methods. Reaction of either of these precursors with 18F - resulted in the formation of 3,5-O-benzylidene-6-deoxy-O-[ 18F]-fluoro-1,2-O-isopropylidene-α-D-glucofuranose in high yield. Subsequent hydrolysis resulted in the production of [18F]6FDG. Under optimal conditions, [18F]6FDG is produced 60-70 min after end of bombardment (EOB) in 71 ± 12% yield (decay corrected, based upon fluoride) with a radiochemical purity of ≥96%. Preliminary experiments have indicated that [18F]6FDG may be a more representative in vivo tracer for the glucose transporter than 2FDG. Copyright
- Neal, Timothy R.,Schumann, William C.,Berridge, Marc S.,Landau, Bernard R.
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p. 845 - 854
(2007/10/03)
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