803631-73-4

Upstream product

• 409113-12-8 (2R,1'R)-ethyl 2-(p-methoxyphenylamino)-2-(2'-oxocyclohex-1'-yl)-acetate 
• 409113-10-6 (3R,3aR,7aR)-hexahydro-3-(p-methoxyphenylamino)-2(3H)-benzofuranone 

Downstream Products

• 96217-48-0 (RS)-amino-((1RS)-trans-2-hydroxy-cyclohexyl)-acetic acid ethyl ester 
• 90205-41-7 (RS)-amino-((1RS)-trans-2-hydroxy-cyclohexyl)-acetic acid 

Relevant academic research and scientific papers

Stereoselective synthesis of enantiopure cycloalkylglycines by 1,3-dipolar cycloaddition of a chiral nitrone to cycloalkenes

The design of cyclic analogues of 4-hydroxyisoleucine, a natural remedy used by type-2 diabetic patients, can provide putative hypoglycemic drugs. To this end, the 1,3-dipolar cycloaddition of a (-)-menthone-derived nitrone to cycloalkenes afforded isoxazolidines in high yields and with high stereoselectivity. The cycloadducts led to α-amino lactones after a one-pot cleavage of the N-O, amide, and N-C-N bonds. Subsequent base-catalyzed hydrolysis provided enantiopure cycloalkylglycine derivatives in good overall yields (>40%) in three simple synthetic steps from the menthone-based chiral nitrone. The conformational analysis of these analogues by DFT calculations highlight some interesting features of the volume occupied by the cycloalkyl residues in comparison to that occupied by the natural 4-hydroxyisoleucine. The 1,3-dipolar cycloaddition of a (-)-menthone-derived nitrone to cycloalkenes afforded isoxazolidines in high yields and with high stereoselectivity. After a one-pot cleavage of the N-O, amide, and N-C-N bonds, the cycloadducts led to α-amino lactones. Subsequent hydrolysis provided enantiopure cycloalkylglycine derivatives in good overall yields (>40%).

NOVEL GLUCAGON-LIKE PEPTIDE 1 MODULATOR AND USES THEREOF

Disclosed herein are novel glucagon-like peptide-1 (GLP-1) modulators and their uses in manufacturing medicaments for the treatment and/or prophylaxis of diseases and/or disorders associated with hyperglycemia.

Cyclic a-amino-y hydroxyamide compounds

Compound of formula (I): wherein: represents an optionally substituted saturated carbon ring having from 4 to 8 ring members, R1 and R4, which may be identical or different, each represents hydrogen or acyl, R2 and R3, which may be identical or different, each represents hydrogen or alkyl, R5 and R6, which may be identical or different, each represents hydrogen or alkyl, or R5 and R6 together, with the nitrogen atom carrying them, form an optionally substituted nitrogen-containing heterocycle, stereoisomers thereof, and also addition salts thereof with a pharmaceutically acceptable acid. Medicinal products containing the same which are useful for treatment of glucose intolerance or of disorders associated with hyperglycemia.

A highly enantioselective amino acid-catalyzed route to functionalized α-amino acids

The development of syntheses providing enantiomerically pure α-amino acids has intrigued generations of chemists and been the subject of intense research. This report describes a general approach to functionalized α-amino acids based on catalytic asymmetr