Novel N-modified glycines based on a (1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol skeleton: 1,3-dioxanes and tripodands

Add time:08/28/2019    Source:sciencedirect.com

Starting from (1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol (p-nitrophenylserinol, a waste optical antipode product from chloromycetin production) or its 5-amino-1,3-dioxane derivatives, we report preliminary data concerning the conversion of these optically active substrates into novel N-modified glycines by chemoselective N-monoalkylation with haloacetic ester or acid (X-CH2COOR, X: Cl, Br; R: Et, H) reagents. The results are discussed in terms of the starting material nature (cyclic vs. acyclic), the steric hindrance in the C-substituted 5-amino-1,3-dioxanes determining the reactivity of the amino-group and the stability of the intermediates. The synthesis of the first tripodands incorporating N-modified glycine motifs as peripheral units is also reported.

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