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- W2079180584 abstract "A new method for the synthesis of glycosyl fluorides under very mild conditions in a homogeneous system is described. When glycosyl chlorides (1–4) are mixed with silver tetrafluoroborate in anhydrous ether, reaction occurs immediately and anomeric mixtures of glycosyl fluorides are obtained in good yield. Changing the solvent to toluene results in anomerization and the preponderant formation of α-d-glucosyl fluorides. An unexpected result was obtained in the reaction of 2,3,4,6-tetra-O-acetyl-α-d-glucopyranosyl chloride with silver tetrafluoroborate in ether. After a short period of reaction 2,3,4,6-tetra-O-acetyl-α- (48%) and -β-d-glucopyranosyl fluorides (33%) were obtained, but 1,2-O-acetoxonium-3,4,6-tri-O-acetyl-α-d-glucopyranose tetrafluoroborate could not be obtained. After a longer period, only 2,3,4,6-tetra-O-acetyl-α-d-glucopyranosyl fluoride was obtained, in 81.5% yield. Similar results were obtained when 1,2-O-acetoxonium-3,4,6-tri-O-acetyl-α-d-glucopyranose tetrafluoroborate was treated with anhydrous ether." @default.
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- W2079180584 date "1970-04-01" @default.
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- W2079180584 title "Reaction of glycosyl chlorides with silver tetrafluoroborate" @default.
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- W2079180584 doi "https://doi.org/10.1016/s0008-6215(00)84893-4" @default.
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