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Synthesis of Phosphinic Isosteres of Leucyl- and Isoleucylglycines

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Abstract

Phosphinic isosteres of leucylglycine and isoleucylglycine were obtained by amidoalkylation of (3-benzyloxy-3-oxopropyl)phosphonous acid bearing the structural isostere fragment of glycine benzyl ester in acetyl chloride. A three-component amide version of the Kabachnik–Fields reaction involving methyl (benzyl) carbamates and 2(3)-methylbutanals was studied. The reaction proceeded under the conditions of acylation of the starting (3-benzyloxy-3-oxopropyl)phosphonous acid and in situ generation of a bisacetyl derivative of the three-coordinated phosphorus, the formation of which was detected using NMR 31Р.

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Funding

A part of the work was carried out within the framework of the governmental task of the Institute of Physiologically Active Substances of the Russian Academy of Sciences (no. 0090-2019-0008) with partial financial support from the Russian Foundation for Basic Research (grant nos. 18-03-00959, 18-03-01123).

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Correspondence to V. V. Ragulin.

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Golovash, S.R., Dmitriev, M.E., Shestov, V.I. et al. Synthesis of Phosphinic Isosteres of Leucyl- and Isoleucylglycines. Russ J Gen Chem 90, 1636–1640 (2020). https://doi.org/10.1134/S107036322009008X

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