121506-22-7Relevant academic research and scientific papers
Practical preparation of α-hydroxy-β-amino ester units; Stereoselective synthesis of taxol side chain and norstatine
Hattori, Kouji,Yamamoto, Hisashi
, p. 2785 - 2792 (1994)
An asymmetric reaction of chiral imines with α-silyloxy ketene acetals mediated by chiral boron reagents is described. The key to its success is the use of the chiral boron complex prepared in situ from (R)- or (S)-binaphthol and B(OPh)3. Both diastereomers of α-hydroxy-β-amino ester units are successfully prepared with high selectivities by the chiral boron reagents depending on the geometry of the silyl ketene acetals. The optically pure anti α-hydroxy-β-amino ester is obtained from (E)-silyl ketene acetal, while the corresponding syn α-hydroxy-β-amino ester is obtained from (Z)- silyl ketene acetal. The method can be efficiently applied to the stereoselective synthesis of taxol C-13 side chain and the norstatine family.
Stereocontrolled asymmetric synthesis of α-hydroxy-β-amino acids. A stereodivergent approach
Aoyagi,Jain,Williams
, p. 3472 - 3477 (2007/10/03)
The stereocontrolled asymmetric synthesis of α-hydroxy-β-amino acids has been investigated via the Lewis acid-promoted cyanation of (5R,6S)-2-acetoxy-4-(benzyloxycarbonyl)-5, 6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazines with trimethylsilyl cyanide. Base-
Process for the production of chiral hydroxy-β-lactams and hydroxyamino acids derived therefrom
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, (2008/06/13)
The reaction between a hydroxyacetic acid derivative bearing an oxygen protecting group and a chiral auxiliary group and an imine produces chiral β-lactams. Hydrolysis of the chiral β-lactams produces chiral amino acid analogs.
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 Stereoselective Synthesis of the (2R,3S)- and (2S,3R)-3-Amino-2-hydroxybutyric Acid Derivatives, the Key Components of a Renin Inhibitor and Bestatin
Kobayashi, Yuko,Takemoto, Yoshiji,Kamijo, Tetsuhide,Harada, Hiromu,Ito, Yoshio,Terashima, Shiro
, p. 1853 - 1868 (2007/10/02)
The title synthesis was achieved by featuring the -cycloaddition reaction of benzyloxyketene with a chiral imine derived from methyl (R)- or (S)-mandelate, alcoholysis of the formed 3,4-cis disubstituted β-lactam under acidic conditions, and reductiv
New and efficient routes to norstatine and its analogs with high enantiomeric purity by β-Lactam Synthon Method
Ojima, Iwao,Park, Young Hoon,Sun, Chung Ming,Brigaud, Thierry,Zhao, Mangzhu
, p. 5737 - 5740 (2007/10/02)
Norstatine and its analogs, i.e., 3-amino-2-hydroxyalkanoic acids, with high enantiomeric purity are obtained through effecient asymmetric synthesis of 3-silyloxy-β-lactams by chiral enolate - imine cyclocondensation, followed by hydrolysis.
Novel synthesis of three types of C-terminal components of renin inhibitors from unnatural (2S,3S)-tartaric acid
Kobayashi,Matsumoto,Takemoto,Nakatani,Ito,Kamijo,Harada,Terashima
, p. 2550 - 2555 (2007/10/02)
The addition reaction of cyclohexylmethylmagnesium bromide with the imine prepared from unnatural (2S,3S)-tartaric acid was found to proceed in a highly stereoselective manner in the presence of cerium(III) chloride. A chelation-controlled mechanism could
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
Orally Potent Human Renin Inhibitors Derived from Angiotensinogen Transition State: Design, Synthesis, and Mode of Interaction
Iizuka, Kinji,Kamijo, Tetsuhide,Herada, Hiromu,Akahane, Kenji,Kubota, Tetsuhiro,et al.
, p. 2707 - 2714 (2007/10/02)
A three-dimensional structure of the complex of human renin and the scissile site P4 Pro to P1' Val of angiotensinogen was deduced in order to design potent human renin inhibitors rationally.On the basis of this structure, an orally
