116315-73-2Relevant academic research and scientific papers
Synthesis of (+)-methyl (R,E)-6-benzyloxy-4-hydroxy-2-hexenoate and its mesylate derivative
De March,Figueredo,Font,Monsalvatje
, p. 331 - 342 (2007/10/02)
Methyl (E)-6-benzyloxy-4-hydroxy-2-hexenoate is prepared in both racemic and enantiopure form through reaction between (2-benzyloxy)ethyloxirane and the dianion of phenylselenoacetic acid followed by esterification with diazomethane, oxidation to the selenoxide and subsequent pyrolysis in 72% overall yield.
SYNTHESES OF α-(R)-AND α-(S)-LIPOIC ACID FROM (S)-MALIC ACID
Brookes, Michael H.,Golding, Bernard T.,Hudson, Alan T.
, p. 9 - 12 (2007/10/02)
(S)-Malic acid has been converted into α-(R)-and α-(S)-lipoic acid via (R)-and (S)-(2-phenylmethoxyethyl)oxirane .The (R)-oxirane (2a) was cleaved with but-3-enylmagnesium bromide (cuprate catalysis) to give (S)-1-(phenylmethoxy)oct-7-en-3-ol (4a).This was converted into methyl (S)-6,8-dihydroxyoctanoate (5a), the di-O-methanesulphonate (6a) of which was treated with sodium sulphide and sulphur in dimethylformamide to yield methyl α-(R)-lipoate (7a), that was saponified to α-(R)-lipoic acid (1a).The (S)-oxirane (2b) was similarly converted into α-(S)-lipoic acid (1b).
