Confirmation of the C-17 stereochemistry of pentolame by single crystal x-ray analysis of its monohydrate

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Autore principale: Cristina Lemini
Natura: Artículo científico
Lingua:en
Pubblicazione: Sociedad Química de México 2004
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author Cristina Lemini
author_facet Cristina Lemini
contents Confirmation of the C-17 stereochemistry of pentolame by single crystal x-ray analysis of its monohydrate Cristina Lemini Ruth Jaimez Rubén A. Toscano Multidisciplinaria (Ciencias Naturales y Exactas) 17 amino estrogen Pentolame ray analysis The molecular and crystal structure of Pentolame, a 17β-aminoestrogen (17β-(5’-hydroxy-1’-pentylamino)-1,3,5(10)-estratrien-3-ol), has been determined by single crystal X-ray diffraction asits monohydrate. The structure was used to determine the absoluteconfiguration of the newly formed stereogenic centre (C17), whichcould not be established unambiguously by NMR spectroscopy. Thisstudy confirms the absolute configuration as 17S by internal referencewith the starting material, estrone [(8R,9S,13S,14S)-3-Hydroxyestra-1,3,5(10)-trien-17-one]. Pentolame monohydrate crystallizes in thetriclinic system, space group P 1 with Z = 1. The B ring adopts thetypical conformation of a distorted 7α,8β-half-chair. In crystalpacking, the water molecule plays an essential role joining adjacentinfinite chains, made up by head to tail hydrogen bonded steroidmolecules. 2004 artículo científico 1870-249X https://www.redalyc.org/articulo.oa?id=47548409 en http://www.redalyc.org/revista.oa?id=475 Journal of the Mexican Chemical Society application/pdf Sociedad Química de México Journal of the Mexican Chemical Society (México) Num.4 Vol.48
format Artículo científico
id redalyc_47548409
institution Redalyc
language en
publishDate 2004
publisher Sociedad Química de México
spellingShingle Confirmation of the C-17 stereochemistry of pentolame by single crystal x-ray analysis of its monohydrate
Cristina Lemini
Multidisciplinaria (Ciencias Naturales y Exactas)
17
amino
estrogen
Pentolame
ray analysis
Confirmation of the C-17 stereochemistry of pentolame by single crystal x-ray analysis of its monohydrate Cristina Lemini Ruth Jaimez Rubén A. Toscano Multidisciplinaria (Ciencias Naturales y Exactas) 17 amino estrogen Pentolame ray analysis The molecular and crystal structure of Pentolame, a 17β-aminoestrogen (17β-(5’-hydroxy-1’-pentylamino)-1,3,5(10)-estratrien-3-ol), has been determined by single crystal X-ray diffraction asits monohydrate. The structure was used to determine the absoluteconfiguration of the newly formed stereogenic centre (C17), whichcould not be established unambiguously by NMR spectroscopy. Thisstudy confirms the absolute configuration as 17S by internal referencewith the starting material, estrone [(8R,9S,13S,14S)-3-Hydroxyestra-1,3,5(10)-trien-17-one]. Pentolame monohydrate crystallizes in thetriclinic system, space group P 1 with Z = 1. The B ring adopts thetypical conformation of a distorted 7α,8β-half-chair. In crystalpacking, the water molecule plays an essential role joining adjacentinfinite chains, made up by head to tail hydrogen bonded steroidmolecules. 2004 artículo científico 1870-249X https://www.redalyc.org/articulo.oa?id=47548409 en http://www.redalyc.org/revista.oa?id=475 Journal of the Mexican Chemical Society application/pdf Sociedad Química de México Journal of the Mexican Chemical Society (México) Num.4 Vol.48
title Confirmation of the C-17 stereochemistry of pentolame by single crystal x-ray analysis of its monohydrate
topic Multidisciplinaria (Ciencias Naturales y Exactas)
17
amino
estrogen
Pentolame
ray analysis
url https://www.redalyc.org/articulo.oa?id=47548409