Phenylglycidic acid

The a carbon of mandelic acid is sp hybridized. The corresponding carbons of both a-phenylglycidic acid, 49, and the carbanion intermediate 48 are neither sp hybridized nor sp hybridized, but presumably between these two extremes. It is therefore possible that the a-phenylglycidic acid is restricted to a conformation which resembles a transition state in the racemization process, a transition state which would have much of the character of the intermediate 48, and for which the enzyme would presumably have a high affinity (1). 

Figure 9. Optical resolution of 3-phenylglycidic acid methyl ester (MPGM) by lipase and separation of the optically active product, (-)-MPGM, from unnecessary acid using Hollow-Fiber membrane reactor...

H Matsumae, M Furui, T Sabatani. Lipase-catalyzed asymmetric hydrolysis of 3-phenylglycidic acid ester, the key intermediate in the synthesis of diltiazem hydrochloride. J Ferment Bioeng 75 93-98, 1993. 

METHYL-3-PHENYLGLYCIDIC ACID ETHYL ESTER see ENCOOO... 

On irradiation, the sodium salt of phenylglycidic acid gives phenylacetaldehyde as the primary product (Eq. 361). ... 

H. Matsumae, T. Shibatani, Purification and characterization of the lipase from Serratia marcescens Sr41 8000 responsible for asymmetric hydrolysis of 3-phenylglycidic acid esters, J. Ferment. Bioeng. 1994, 77, 152-158. 

Synonyms cas 77-83-8 C-ie aldehyde EMPG a-p-EPOXY-p-METHYLHYDROCINNAMIC acid, ethyl ester ETHYLa,p-EPOXY-p-METHYLHYDROCINNAMATE ETHYL 2,3-EP0XY-3-METHYL-3-PHENYLPR0PI0NATE ETHYL ESTEROf 2,3-EPOXY-3-PHENYLBUTANOIC ACID FRAESEOL 3-METHYL-3-PHENYLGLYCIDIC ACID ETHYL ESTER STRAWBERRY ALDEHYDE... 

Matsumae H, Furui M, Shibatani T, Tosa T (1994), Production of optically active 3-phenylglycidic acid ester by the lipase from Serratia marcescens on a hollow-fiber membrane reactor ,/. Ferment. Bioeng., 78,59-63. 

Darzens condensation of an aromatic aldehyde with a-bromo-y-valero-lactone has been used in the preparation of ketides. The acid-catalysed decarboxylation of a-phenylglycidic acids is reported to give abnormal products a non-concerted mechanism involving oxiran ring-opening is invoked. a-Halogenoglycidic esters can be obtained by reaction of tris(di-methylamino)phosphine with trichloroacetic acid derivatives in the presence of carbonyl compounds (Scheme 18) cyclohexanone affords the isomeric halogenated pyruvic acid derivative (51) in quantitative yield. ... 

Phenoxymethylanhydropenicillin, Y29 Phenylalanine, AS A -phenylalanine, A13 jS-phenylglycidic acid, A19 Phenyl ycine, A23 Phenylserine, A19 ]3-phenylserine, A21 Phenylisoserines, A19, A8 Phenyltetrahydroisoquinoline alkaloids, K1 Phomenone, T7 ... 

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