Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Acetonation of L-Sorbose by Ketal Interchange
Takashi Maeda
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1967 Volume 40 Issue 9 Pages 2122-2128

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Abstract

The acetonation reaction of L-sorbose with acetone dimethyl ketal was investigated. The products and the yields were greatly influenced by the reaction conditions. The reaction at 45°C gave 1, 3 : 4, 6-di-O-isopropylidene-β- (VIIa), 1, 2 : 4, 6-di-O-isopropylidene-α- (Va) and 2, 3 : 4, 6-di-O-isopropylidene-α-L-sorbofuranose (IVa) and the β-anomer of Va (VIa). At the refluxing temperature, the reaction afforded IVa and the 2-O-methyl derivative of VIIa (VIIe), while at room temperature it yielded 1, 2 : 3, 4-di-O-isopropylidene-α-L-sorbopyranose (VIIIa), 1, 2 : 4, 5-di-O-isopropylidene-α-L-sorbopyranose (IXa), and 5-O-α-methoxyisopropyl-1, 2 : 3, 4-di-O-isopropylidene-α-L-sorbopyranose (VIIIc).

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