Asymmetric syntheses of highly hydrophobic chimeric aromatic amino acids: 2-Amino-3,3'-diarylpropionic acids

Tetrahedron Letters

Volumn 39, Issue 20, 1998, Pages 3117-3120

  Lin, Jun ^a,b   Liao, Subo ^a,c   Hruby, Victor J ^a  

^a University of Arizona   (United States)

^b YUNNAN UNIVERSITY   (China)

^c Selectide Corporation   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 3,3' DIARYLPROPIONIC ACID; AROMATIC AMINO ACID; UNCLASSIFIED DRUG;

AMINO ACID SYNTHESIS; ARTICLE; CHIRALITY; CONFORMATIONAL TRANSITION; HYDROPHOBICITY; LIGAND BINDING; PROTEIN BINDING; PROTEIN CONFORMATION; SIGNAL TRANSDUCTION; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0032516376     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00516-4     Document Type: Article

References (18)

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16. 7. The azidation yield was significantly improved when 1:1 KHMDS/NaH was used as base.
17. 8. Procedure to cleave the chiral auxiliary: After the cleavage of azido derivative 6, the reaction mixture was acidified with 6N HCl, the organic phase was separated, and the aqueous phase was extracted with DCM. The combined organic phases were washed, dried and evaporated. Then hexanes/ethyl acetate (7:3) was added to precipitate and recover the auxiliaries. The mother liquid was evaporated and the residue was purified by column chromatography with chloroform/methanol (5:1) to give the desired azido acid 7.
18. 22 = -56.8 (c = 0.50, MeOH).