Synthesis of (S)-α-amino oleic acid

dc.contributor.author	Magrioti, V	en
dc.contributor.author	Constantinou-Kokotou, V	en
dc.date.accessioned	2014-06-06T06:45:09Z
dc.date.available	2014-06-06T06:45:09Z
dc.date.issued	2002	en
dc.identifier.issn	00244201	en
dc.identifier.uri	http://62.217.125.90/xmlui/handle/123456789/2274
dc.relation.uri	http://www.scopus.com/inward/record.url?eid=2-s2.0-0036198701&partnerID=40&md5=bea807b39ff6b486795b1f538ad881c6	en
dc.subject.other	Aldehydes	en
dc.subject.other	Hydrogenation	en
dc.subject.other	Reduction	en
dc.subject.other	Saponification	en
dc.subject.other	Double bonds	en
dc.subject.other	Oleic acid	en
dc.subject.other	aldehyde	en
dc.subject.other	alkene	en
dc.subject.other	alpha amino oleic acid	en
dc.subject.other	aminoalcohol	en
dc.subject.other	ester	en
dc.subject.other	fatty acid derivative	en
dc.subject.other	methyl 2 [bis(tert butoxycarbonyl)amino] 5 oxopentanoate	en
dc.subject.other	oleic acid	en
dc.subject.other	phosphonic acid derivative	en
dc.subject.other	unclassified drug	en
dc.subject.other	amino acid synthesis	en
dc.subject.other	article	en
dc.subject.other	chemical bond	en
dc.subject.other	chemical reaction	en
dc.subject.other	hydrogenation	en
dc.subject.other	reaction analysis	en
dc.subject.other	saponification	en
dc.subject.other	spectroscopy	en
dc.subject.other	structure analysis	en
dc.subject.other	Chromatography, Thin Layer	en
dc.subject.other	Magnetic Resonance Spectroscopy	en
dc.subject.other	Oleic Acid	en
dc.title	Synthesis of (S)-α-amino oleic acid	en
heal.type	journalArticle	en
heal.publicationDate	2002	en
heal.abstract	An efficient synthesis of (S)-α-amino oleic acid was developed. The fully protected FA derivative was obtained in four steps starting from methyl (2S)-2-[bis(tert-butoxycarbonyl)amino]-5-oxopentanoate. These steps are (i) olefination of the starting aldehyde with the appropriate phosphonate anion, (ii) hydrogenation of the double bonds, (iii) controlled reduction of ω-ethyl ester to an aldehyde in the presence of αmethyl ester, and (iv) a Wittig reaction of the latter aldehyde with the suitable ylide. Free α-amino oleic acid was prepared after deprotection of the amino group followed by saponification in a total yield of 24%. N-tert-Butoxycarbonyl-protected amino oleic acid and the corresponding amino alcohol were prepared in high yield. The structures of the products have been established by various spectroscopic techniques.	en
heal.journalName	Lipids	en
dc.identifier.issue	2	en
dc.identifier.volume	37	en
dc.identifier.spage	223	en
dc.identifier.epage	228	en