165058-77-5Relevant academic research and scientific papers
Enantioselective synthesis of homosphingosine derivatives from L-aspartic acid
Sauerland, Sami J.K.,Castillo-Melendez, Joel A.,Naettinen, Kalle,Rissanen, Kari,Koskinen, Ari M.P.
, p. 757 - 762 (2010)
The sterically demanding 9-phenylfluorenyl N-protection of a number of amino acids allows the formation of amino acid derived β-ketophosphonate reagents and their Horner-Wadsworth-Emmons olefination. In an attempt to develop a synthesis of D-erythro-homosphingosine in enantiopure form, we have shown that the reactivity of the intermediates is influenced by the distinctive conformational requirements of this large protecting group. Georg Thieme Verlag Stuttgart · New York.
Syntheses of optically active, protected and unprotected vinylglycines
Itaya,Shimizu,Nakagawa,Morisue
, p. 1927 - 1930 (2007/10/02)
Vinylglycine (2) has been shown to undergo racemization under acidic conditions. Optically pure 2 was obtained from 2 · HCl by enzymatic hydrolysis through N-acetylvinylglycine (5), followed by recrystallization. (S)N-(Methoxycarbonyl)vinylglycine (6) was configurationally so unstable under acidic conditions that 6 could not be obtained from 2 in an optically pure form. On the other hand, configurationally stable (S)-N-(9-phenylfluoren-9-yl)vinylglycine methyl ester (9) was synthesized from (S)-homoserine; 9 was hydrolyzed with sodium hydroxide to afford the carboxylic acid 10 of more than 99% ee.
