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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 |
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