Asymmetric synthesis with sugar derivatives. 3. Action of methylmagnesium iodide on sugar esters of phenylglyoxylic acid.

doi:10.1246/BCSJ.40.2168

Paper

Asymmetric synthesis with sugar derivatives. 3. Action of methylmagnesium iodide on sugar esters of phenylglyoxylic acid.

Published Sep 1, 1967 · M. Kawana, S. Emoto

Bulletin of the Chemical Society of Japan

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7

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0

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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.

Study Snapshot

Methylmagnesium iodide effectively synthesizes atrolactic acid from sugar esters of phenylglyoxylic acid, yielding levorotatory acid in 22-38% optical yield.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Asymmetric synthesis with sugar derivatives. 3. Action of methylmagnesium iodide on sugar esters of phenylglyoxylic acid.

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References

Asymmetric Synthesis with Sugar Derivatives. II. Asymmetric Syntheses by Methoxy-Mercuration of Cinnamic Esters of Sugar Derivatives

Methoxy-mercuration of cinnamic esters of sugar derivatives can produce 3-methoxy-3-phenylpropionic acid (V) and 3-methoxy-3-phenylpropan-1-ol (IX) in varying optical yields, with the absolute configurations

Asymmetric Synthesis with Sugar Derivatives. I. The Conjugate Additions of Grignard Reagents to α, β-Unsaturated Esters of Sugar Derivatives

Asymmetric synthesis of sugar derivatives using Grignard reagents can yield (+)-acid (III) and ()-acid (III) in high yields, with potential applications in pharmaceutical synthesis.

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