124947-31-5Relevant academic research and scientific papers
FLUOROUS OXAZOLIDINONE CHIRAL AUXILIARY COMPOUNDS AND METHODS OF MANUFACTURE
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Page/Page column 7, (2008/06/13)
The present invention relates generally to perfluoroalkyl chiral auxiliary compounds and methods of manufacture. These compounds have the functionality to effectively support the synthesis of chiral compounds in single reactions, high-throughput parallel recations, or combinatorial reactions The invention relates to two oxazolidmone chiral auxiliaries (1) and (2): wherein Rf is a perfluoroalkyl group having the general formula (CH2)x-CyF2y+1 where x = 1-5 and y = 4-10 and wherein B is an unfunctionalized aryl, alkyl or arylalkyl group Pn a preferred embodiment, x = 2 and y = 6 and B is derived from unfunctionalized ammo acids The ammo acids may be from either the D- or L- series, and are preferably enantiomeπcally pure or in very high enantiomeric excess in either configuration.
Practical synthesis of fluorous oxazolidinone chiral auxiliaries from α-amino acids
Hein, Jason E.,Geary, Laina M.,Jaworski, Ashley A.,Hultin, Philip G.
, p. 9940 - 9946 (2007/10/03)
A series of new fluorous-supported oxazolidinone chiral auxiliaries has been prepared using a versatile and general five-step pathway, starting from readily available chiral α-amino acids. The key feature of this synthesis is the efficient generation of a suitably active perfluoroalkyllithium species. By use of this protocol, the auxiliaries can be obtained in high enantiomeric purity and on multigram scales from L-phenylalanine and L-valine with overall yields as high as 55%. The new methodology also incorporates fluorous solid-phase extraction on the large scale, allowing bulk quantities (up to 25 g) of fluorous compounds to be purified from the crude reaction mixture.
A Practical Synthesis of threo-3-Amino-2-hydroxycarboxylic Acids
Matsuda, Fuyuhiko,Mtsumoto, Teruyo,Ohsaki, Masako,Ito, Yoshio,Terashima, Shiro
, p. 360 - 365 (2007/10/02)
An expeditious synthesis of (2R,3S)-3-amino-4-cyclohexyl-2-hydroxybutyric acid (2) and (2S,3R)-3-amino-2-hydroxy-4-phenylbutyric acid (4), the key components of the renin inhibitor (1) and bestatin (3), respectively, have been accomplished by featuring hi
A highly stereoselective synthesis of (3S,4S)-statine and (3S,4S)-cyclohexylstatine
Takemoto,Matsumoto,Ito,Terashima
, p. 2425 - 2428 (2007/10/02)
The title compounds, which are synthetic intermediates of renin inhibitors, could be prepared from (S)-leucine and (S)-phenylalanine, respectively, by employing highly stereoselective aldol reactions of O-methyl-O-trimethylsilyl ketene acetal with an (S)-
A Practical Synthesis of an Orally Potent Renin Inhibitor, Isopropyl (2R,3S)-4-Cyclohexyl-2-hydroxy-3--L-histidyl>aminobutyrate
Harada, Hiromu,Iyobe, Akira,Tsubaki, Atsushi,Yamaguchi, Toshiaki,Hirata, Kazuma,et al.
, p. 2497 - 2500 (2007/10/02)
The practical synthesis of an orally potent human renin inhibitor, isopropyl (2R,3S)-4-cyclohexyl-2-hydroxy-3--L-histidyl>aminobutyrate, is presented.Optically pure cyclohexylnorstatine isopropyl
An expeditious synthesis of (3S,4S)-statine and (3S,4S)cyclohexylstatine
Takemoto, Yoshiji,Matsumoto, Teruyo,Ito, Yoshio,Terashima, Shiro
, p. 217 - 218 (2007/10/02)
The title synthesis could be accomplished by employing highly stereoselective aldol reaction of O-methyl-O-trimethylsilyl ketene acetal with the (S)-α-amido aldehyde (2) in the presence of titanium (IV) chloride as a key step.
