72155-54-5Relevant academic research and scientific papers
Enantiospecific Synthesis of (3S,4S)-Statine and Its Analogue from D-Glucosamine as a Chiral Pool
Shinozaki, Katsuo,Mizuno, Kazuhiro,Oda, Hirohisa,Masaki, Yukio
, p. 2265 - 2268 (1992)
The C(6)-carbon degradation and elimination C(4)-hydroxy group of D-glucosamine were achieved in 8-steps and 30percent overall yield to furnish (4R,5S)-5-vinyl-2-oxazolidinone-4-carbaldehyde dimethyl acetal, which was utilized as a key intermediate for en
Synthesis of (3S,4S)-statine and a related compound, (3S,4S)-AHPPA, from D-glucosamine as a chiral pool
Shinozaki, Katsuo,Mizuno, Kazuhiro,Oda, Hirohisa,Masaki, Yukio
, p. 1737 - 1745 (2007/10/03)
Biologically important threo-β-hydroxy-γ-amino acids, (3S,4S)-statine ((3S,4S)-4-amino-3-hydroxy-6-methylheptanoic acid) (1) and (3S,4S)-AHPPA (3S,4S)-4-amino-3-hydroxy-5-phenylpentanoic acid) (2), were synthesized starting from D-glucosamine (3) as a chiral pool. Two routes for the transformation of D-glucosamine to key intermediates, which are applicable to the synthesis of threo-β-hydroxy-γ-amino acids, were investigated. The successful route involved C(6)-carbon degradation and elimination of the C(4)-hydroxy group of D-glucosamine in 8 steps and 30% overall yield to furnish (4R,5S)-2-oxo-5-vinyloxazolidine-4-carbaldehyde dimethyl acetal (17), which has been utilized as a versatile intermediate for synthesizing the target compounds.
Synthesis of analogues of the carboxyl protease inhibitor pepstatin. Effect of structure on inhibition of pepsin and renin
Rich,Sun,Ulm
, p. 27 - 33 (2007/10/02)
Analogues of the carboxyl protease inhibitor, pepstatin, were synthesized from optically pure forms of N-(tert-butoxycarbonyl)-4-amino-3-hydroxy-6-methylheptanoic acid (Boc-Sta), and the inhibition of pepsin and renin was determined. In addition, the new
