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- W2067156792 startingPage "1838" @default.
- W2067156792 abstract "Diethyl or dimethyl benzyloxycarbonylaminomalonate was reacted with ring substituted benzyl halides and the resulting arylalkyl derivatives (3 to 6) half-saponified to the DL-monoacid-monoesters (7 to 10). Decarboxylation by refluxing in dioxane afforded the N-benzyl oxycarbonyl-DL-amino acid esters (11 to 14), which were resolved into their optical antipodes by enzymic hydrolysis of the ester group with Subtilisin, type Carlsberg. Enzymic hydrolysis led to the N-benzyloxycarbonyl-L-amino acids (15 to 18) and to the corresponding D-amino acid esters. The latter were converted to the N-benzyloxycarbonyl-D-amino acids (19 and 20) by alkaline hydrolysis of the ester groups. These derivatives could be used directly for further peptide synthesis. The following compounds were prepared: N-benzyloxycarbonyl derivatives of p-methyl-L-phenylalanine (15), p-methyl-D-phenylalanine (19), p-fluoro-L-phenylalanine (16), m-fluoro-L-phenylalanine (17), m-fluoro-D-phenylalanine (20) and penta-fluoro-L-phenylalanine (18). The free amino acids were obtained by removal of the benzyloxycarbonyl group with HBr in acetic acid." @default.
- W2067156792 created "2016-06-24" @default.
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- W2067156792 date "1973-07-18" @default.
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- W2067156792 title "Synthesis of Optically Active, Ring-Substituted N-Benzyloxycarbonylphenylalaninesvia 2-Benzyloxycarbonylamino-2-arylalkylmalonates" @default.
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- W2067156792 doi "https://doi.org/10.1002/hlca.19730560603" @default.
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