Synthesis of 6-O-Acetyl-α-Glucose

Abstract

β-GLUCOSE pentaacetate in acetone solution can be partially deacetylated by cooled 1 N potassium hydroxide solution to yield 6-O-acetyl-α-glucose. This product has a melting point of 146°. It has been identified by analysis, molecular-weight determination, downward mutarotation to +53° and hydrolysis to glucose and acetic acid. Periodate oxidation requires 4 moles of periodate per mole 6-O-acetyl-α-glucose without yielding formaldehyde, but glycol-aldehyde as p-nitrophenyl ozazone could be isolated as a product of oxidation. 6-O-acetyl-α-glucose cannot be tritylated, but a phenylosazone of it has been prepared, m.p. 171°.

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FROHWEIN, Y., LEIBOWITZ, J. Synthesis of 6-O-Acetyl-α-Glucose. Nature 186, 153 (1960). https://doi.org/10.1038/186153a0

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