cas 1032237-00-5, (2S,4R)-4-hydroxypiperidine-2-carboxylic acid hydrochloride

Articles about 1032237-00-5Total 3 be found

Enantioselective Synthesis of cis and trans 4-Aminopipecolic Acids as γ-Amino Acids for the Construction of Cyclic RGD-Containing Peptidomimetics Antagonists of αVβ3 Integrin
A stereodivergent strategy to obtain enantiopure cis and trans 4-aminopipecolic acids (4-APAs) in a suitably protected form for peptide synthesis has been devised starting from a common, known precursor in turn easily prepared from commercial (R)-4-cyano-3-hydroxybutyric acid ethyl ester. The two isomers were efficiently obtained in 40 percent and 23 percent overall yields, respectively, in seven and ten steps. To demonstrate their usefulness in peptidomimetic synthesis, both 4-APA isomers were incorporated as γ-amino acids in a cyclic RGD-containing sequence, although for the trans 4-APA isomer a further amino acid in the sequence (L-Phe) was needed to allow ring closure. The two cyclopeptides were tested as αVβ3 integrin antagonists in comparison with cilengitide.
Bianchini, Francesca,Contini, Alessandro,Dordoni, Francesca,Occhiato, Ernesto G.,Scarpi, Dina
(2020)
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A short and convenient synthesis of enantiopure cis- And trans-4-hydroxypipecolic acid
The synthesis of (2S,4R)- and (2R,4R)-4-hydroxypipecolic acid has been realized from commercial ethyl (R)-4-cyano-3hydroxybutanoate through palladium-catalyzed methoxycarbonylation of a 4-hydroxy-substituted lactam-derived vinyl phosphate followed by the
Occhiato, Ernesto G.,Scarpi, Dina,Guama, Antonio,Tabasso, Silvia,Deagostino, Annamaria,Prandi, Cristina
experimental part
p. 3611 - 3616
(2010/03/30)

Stereoselective synthesis of (2S,4R)-4-hydroxypipecolic acid
A new synthetic route to enantiopure (2S,4R)-4-hydroxypipecolic acid from commercial ethyl (3S)-4-chloro-3-hydroxybutanoate is reported. The synthesis is based on the Pd-catalyzed methoxycarbonylation of a 4-alkoxy-substituted δ-valerolactam-derived vinyl triflate followed by the stereocontrolled hydrogenation of the enamine double bond. The final product was obtained after exhaustive hydrolysis in 20 % yield over 10 steps. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Occhiato, Ernesto G.,Scarpi, Dina,Guarna, Antonio
p. 524 - 531
(2008/09/18)