Add time:08/27/2019         Source:sciencedirect.com

An efficient preparation of N-α-Fmoc-4-phosphono(difluoromethyl)-L-phenylalanine 5 is described. The synthesis of this phosphotyrosine isostere involves deprotection of the penultimate diethylphosphonate intermediate 4 with BSTFA/TMSI as the key step. Building block 5 can be utilized directly for incorporation into peptides without protection of the side chain phosphonic acid group, as illustrated by the efficient preparation of model difluorophosphonopeptides Ac-F2Pmp-Ile-Asn-Gln-NH2 and Ac-Glu-F2Pmp-Ile-Asn-Gln-NH2.

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