Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Asymmetric Synthesis with Sugar Derivatives. III. Action of Methylmagnesium Iodide on Sugar Esters of Phenylglyoxylic Acid
Masajiro KawanaSakae Emoto
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1967 Volume 40 Issue 9 Pages 2168-2171

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Abstract

Asymmetric synthesis of atrolactic acid was investigated by the reaction of methylmagnesium Iodide with phenylglyoxylic ester containing such an optically active component as 1,2 ; 5,6-di-O-cyclohexylidene-D-glucose, its isopropylidene derivative 5-O-ethyl-1,2-O-isopropylidene-D-xylose, its 5-deoxy-5-S-ethyl derivative, or 5-deoxy-1,2-O-isopropylidene-D-xylose. All of the resulting sugar atrolactates were very easily hydrolyzed with alkali at room temperature to afford the levorotatory acid in 22–38% optical yield. The asymmetric reactions proceeded in accordance with Prelog’s rule, but a Prelog’s scheme for asymmetric induction was slightly modified when the steric course for 3-O-phenylglyoxyloyl-1,2 ; 5,6-di-O-cyclohexylidene- and -isopropylidene-D-glucose was discussed.

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