44595-48-4Relevant academic research and scientific papers
Lipase-mediated resolution of 3-hydroxy-4-trityloxybutanenitrile: synthesis of 2-amino alcohols, oxazolidinones and GABOB
Kamal, Ahmed,Khanna, G.B. Ramesh,Krishnaji,Ramu
, p. 1281 - 1289 (2007/10/03)
Lipase-mediated kinetic resolution of 3-hydroxy-4-trityloxybutanenitrile gave the (S)-alcohol and (R)-acetate in good yields and high enantioselectivities. The resolution using Pseudomonas cepacia lipase (Burkholderia cepacia) immobilized on modified cera
Synthetic routes to L-carnitine and L-gamma-amino-betahydroxybutyric acid from (S)-3-hydroxybutyrolactone by functional group priority switching
Wang, Guijun,Hollingsworth, Rawle I.
, p. 1895 - 1901 (2007/10/03)
(R)-3-Hydroxy-4-trimethylaminobutyric acid (L-carnitine) and (R)-4- amino-3-hydroxybutyric acid (GABOB) are two compounds with a very high level of medical significance. They can be prepared from (R)-3-hydroxy-γ- butyrolactone which is not readily available in significant quantities. The corresponding (S)-lactone is available in large quantities but attempts at inverting the stereochemistry of the hydroxyl group lead to elimination to give the furanone. Here we describe a straightforward route to these two compounds, starting from (S)-3-hydroxy-γ-butyrolactone by adding a highly oxidized carbon at one end whilst removing one carbon from the other, thus switching the functional group priorities. In this method, the lactone is transformed to an (R)-4-cyano-3-hydroxybutyric acid ester which is then converted to an acyl hydrazide by treatment with hydrazine. This stable, crystalline hydrazide has not been described before. It is readily converted to (R)-4-amino-3-hydroxybutyronitrile, a precursor of L-carnitine and GABOB, by Curtius rearrangement under conditions that do not result in deamination.
