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Journal of the Mexican Chemical Society

Print version ISSN 1870-249X


DE LA CRUZ-CORDERO, Ricardo; LABASTIDA-GALVAN, Victoria; FERNANDEZ-ZERTUCHE, Mario  and  ORDONEZ, Mario. Preparation of Phosphostatine Analogues From L-amino acids. J. Mex. Chem. Soc [online]. 2005, vol.49, n.4, pp.312-321. ISSN 1870-249X.

Reduction of (3S)-N,N-dibenzylamino-2-ketophosphonates 9a-d derived from L-amino acids was carried out with catecholborane at -20 oC to afford the (3S)-N,N-dibenzylammo-(2R)-hydroxy-phosphonates syn-10a-d, whereas the reduction of (3S)-N-benzylamino-2-ketophosphonates 13a-d with Zn(BH4)2 at -78 oC yield (3S)-N-benzylamino-(2S)-hydroxyphosphonates anti-14a-d. The reduction in both cases was in good chemical yields and with high diastereoselectivity. The hydrolysis and hydrogenolysis of 10a-d and 14a-d afford the (3S)-amino-(2R)-hydroxyphosphonic acids 6 and (3S)-amino-(2S)-hydroxyphosphonic acids 7, respectively, which are analogues of phosphostatine.

Keywords : Phosphostatine; aminophosphonic acids; β-ketophosphonates; diastereoselective reduction.

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