60010-78-8Relevant academic research and scientific papers
Method for preparing diastereoisomers of 4-hydroxy isoleucine
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Page/Page column 13, (2008/06/13)
The invention relates to a method for preparing diastereoisomers of 4-hydroxy isoleucine of formula A ????????CO2H- CH(NH2)- CH(CH3)-CH(OH)-CH3?????(A) which comprises the following steps: deprotection of amine of Formula B reduction and subsequent lactonisation of an intermediate amine derivative of formula C whose substituents at positions 2 and 3 are either R, S or S, S ; or S, R or R, R,hydrolysis of the resulting lactone of formula D where in substituents at positions 2, 3 and 4 are S,R,S or S,R,R when using a protected amine S,RS,S,S or S,S,R when using a protected amine S,SR,S,R or R,S,S, when using a protected amine R,SR,R,R or R,R,S when using a protected amine R,R under conditions to obtain the desired isomer of 4-hydroxy isoleucine. Application for preparing the 8 isomeric forms of 4-hydroxy isoleucine.
Compounds and compositions for use in the prevention and treatment of obesity and related syndromes
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Page/Page column 45-46, (2010/11/24)
The invention relates to 4-hydroxyisoleucine, isomers, analogs, lactones, salts, and prodrugs thereof, to processes for their preparation, and to pharmaceutical compositions comprising the same. More particularly, the invention relates to the use of those compounds in the prevention and treatment of obesity and related syndromes.
DIASTEREOISOMERS OF 4-HYDROXYISOLEUCINE AND USES THEREOF
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Page/Page column 30; 1/3, (2008/06/13)
The invention relates to configurational isomers 4-hydroxyisoleucine, and to lactones, pharmaceutically acceptable salts, and prodrugs thereof, to processes for their preparation, and to pharmaceutical compositions comprising the same. The isomers of the invention exhibit insulinotropic activity and thus may be useful for the prevention and treatment of disorders of carbohydrate or lipid metabolism, including diabetes mellitus (type 1 and type 2 diabetes), pre-diabetes, and Metabolic Syndrome.
Organoaluminium induced ring-opening of epoxypyranosides. IV. Synthesis and structure of γ-hydroxy-Isoleucine stereoisomers and their corresponding lactones
Inghardt, Tord,Frejd, Torbjoern,Svensson, Goeran
, p. 6469 - 6482 (2007/10/02)
Two γ-hydroxy-isoleucine stereoisomers 8 (2R, 3R, 4R), and 14 (2S, 3R, 4R) as well as their corresponding γ- lactones 9 and 15 were synthesized using a tandem. Me3Al induced opening of the epoxide and pyranoside rings of benzyl 2,3-anhydro-4-O-(tert-butyldimethylsilyl)-β-L-ribopyranoside (1). The structure of the lactone hydrochloride 9 was confirmed by an X-ray crystal structure determination.
