Preparation of Phosphostatine Analogues From L-amino acids

Please use this identifier to cite or link to this item: http://ri.uaemex.mx/handle20.500.11799/39328

Title:	Preparation of Phosphostatine Analogues From L-amino acids
Keywords:	Química;Phosphostatine;aminophosphonic acids;β-ketophosphonates,;diastereoselective reduction;info:eu-repo/classification/cti/2
Publisher:	Sociedad Química de México
Project:	http://www.redalyc.org/revista.oa?id=475
Description:	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-dibenzylamino-(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.
URI:	http://ri.uaemex.mx/handle20.500.11799/39328
Other Identifiers:	http://hdl.handle.net/20.500.11799/39328
Rights:	info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by-nc-nd/4.0
Appears in Collections:	Producción

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