Preparation of Orthogonally-Protected 3-Methoxy-4-Phosphonomethyl-LPhenylalanine,a New Reagent for the Synthesis of Phosphotyrosyl Mimetic-Containing Peptides

W.J. Choi; S.-U. Kang; T.R. Burke Jr.

doi:10.2174/157017807781467614

Abstract

[(4-Hydroxymethyl-2-methoxyphenyl)methyl]phosphonic acid di-tert-butyl ester (8) served as a key intermediate in the stereoselective preparation of N-Fmoc-3-methoxy-4-(di-tert-butyl)phosphonomethyl-L-phenylalanine (5). Reagent 5 may be useful for the solid-phase synthesis of phosphotyrosyl mimetic-containing peptides.

Keywords: Amino acid, asymmetric, chiral auxiliaries, peptides, stereoselective synthesis

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Letters in Organic Chemistry

Title: Preparation of Orthogonally-Protected 3-Methoxy-4-Phosphonomethyl-LPhenylalanine,a New Reagent for the Synthesis of Phosphotyrosyl Mimetic-Containing Peptides

Volume: 4 Issue: 6

Author(s): W.J. Choi, S.-U. Kang and T.R. Burke Jr.

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Keywords: Amino acid, asymmetric, chiral auxiliaries, peptides, stereoselective synthesis

Abstract: [(4-Hydroxymethyl-2-methoxyphenyl)methyl]phosphonic acid di-tert-butyl ester (8) served as a key intermediate in the stereoselective preparation of N-Fmoc-3-methoxy-4-(di-tert-butyl)phosphonomethyl-L-phenylalanine (5). Reagent 5 may be useful for the solid-phase synthesis of phosphotyrosyl mimetic-containing peptides.

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W.J. Choi , S.-U. Kang and T.R. Burke Jr. , Preparation of Orthogonally-Protected 3-Methoxy-4-Phosphonomethyl-LPhenylalanine,a New Reagent for the Synthesis of Phosphotyrosyl Mimetic-Containing Peptides, Letters in Organic Chemistry 2007; 4 (6) . https://dx.doi.org/10.2174/157017807781467614