Add time:07/11/2019         Source:sciencedirect.com

The original synthesis of 6-deoxy-6-fluoro-D-glucose, which involves as the key stage a fluoride-displacement reaction on 3,5-O-benzylidene-1,2-O-isopropylidene-6-O-mesyl-α-D-glucofuranose, has been improved. Treatment of methyl 6-O-tosyl-α-D-glucopyranoside with potassium fluoride in boiling ethane-1,2-diol affords a mixture of 6-deoxy-6-fluoro and 3,6-anhydro derivatives of D-glucose. The α, β-pyranose equilibrium in aqueous solution is not significantly changed on conversion of D-glucose into the 6-deoxy-6-fluoro derivative. Treatment of 1,2,3,4-tetra-O-acetyl-6-deoxy-6-fluoro-α, β-D-glucopyranose with hydrogen fluoride at - 10° yields, in addition to the expected acetylated α-D-glycosyl fluoride, 3,4-di-O-acetyl-6-deoxy-6-fluoro-α-D-glucopyranosyl fluoride. On the basis of n.m.r. data, the preferred rotamer about the C-5-C-6 bond in 1,2,3,4-tetra-O-acetyl-6-deoxy-6-fluoro-α- and -β-D-glucopyranose and the corresponding glycosyl fluorides was identified as having F-6 and H-5 antiplanar. A 5J FF coupling was observed in each glycosyl fluoride.

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