Synthesis of protected gamma-carboxyglutamates and gamma-acylglutamates by rearrangement of N,N-diacylglutamates |
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| Authors: | Avent Anthony G Duggan Heather M E Young Douglas W |
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| Institution: | Department of Chemistry, University of Sussex, Falmer, Brighton, UKBN1 9QJ. |
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| Abstract: | A new method for gamma-acylation of protected glutamic acids, involving intramolecular rearrangement of an acyl urethane, has been devised to prepare the protected gamma-carboxyglutamates 7, 9 and 11 and the protected 4-acylglutamates 15 and 22 from N,N-bisurethanes or N-acyl-N-urethanes of general structure 1. When the formyl-urethane 17 was used in the reaction, then the intermediate 18 in the intramolecular rearrangement was obtained. |
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