Facile synthesis of optically pure (S)-3-p-hydroxyphenyllactic acid derivatives

Amino Acids

Volumn 33, Issue 3, 2007, Pages 537-541

  Zeng, Q L ^a,c   Wang, H Q ^a   Liu, Z R ^b   Li, B G ^b   Zhao, Y F ^a  

^a XIAMEN UNIVERSITY   (China)

^b Institute of Pharmacy   (China)

^c CHENGDU UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

(S) 3 p Benzyloxyphenylpropionic acid; (S) p Hydroxyphenyllactic acid; Diazotization; O Benzyl L tyrosine; Solvent effects

Indexed keywords

ATROLACTIC ACID; DIMETHYL SULFOXIDE; LACTIC ACID DERIVATIVE; N,N DIMETHYLFORMAMIDE; TYROSINE DERIVATIVE;

ARTICLE; CRYSTALLIZATION; DIAZOTIZATION; DIELECTRIC CONSTANT; PRIORITY JOURNAL; SYNTHESIS;

MOLECULAR CONFORMATION; PHENYLPROPIONATES; SOLVENTS;

EID: 34548313994     PISSN: 09394451     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00726-006-0451-6     Document Type: Article

References (21)

1. Andersson K (1999) WO 99/62872, assigned to Astra Aktiebolag Company
2. JA Dean 1999 Lange's handbook of chemistry 15 McGraw-Hill New York 5.105 5.129
3. HJ Deussen M Zundel M Valdois SV Lehmann V Weil CM Hjort PR Ostergaard E Marcussen S Ebdrup 2003 Process development on the enantioselective enzymatic hydrolysis of S-ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoate Org Process Res Dev 7 82 88
4. D Haigh G Allen HC Birrell DR Buckle BCC Cantello DS Eggleston RC Haltiwanger JC Holder CA Lister IL Pinto HK Rami JT Sime SA Smith JD Sweeney 1999a Non-thiazolidinedione antihyperglycaemic agents. Part 3: The effects of stereochemistry on the potency of α-methoxy-β-phenylpropanoic acids Bioorg Med Chem 7 821 830
5. D Haigh HC Birrell BCC Cantello DS Eggleston RC Haltiwanger RM Hindley A Ramaswamy NC Stevens 1999b Non-thiazolidinedione antihyperglycaemic agents. Part 5: Asymmetric aldol synthesis of (S)-(-)-2-oxy-3-arylpropanoic acids Tetrahedron: Asymmetry 10 1353 1367
6. K Ishida Y Okita H Matsuda T Okino M Murakami 1999 Aeruginosins, protease inhibitors from the cyanobacterium Microcystis aeruginosa Tetrahedron 55 10971 10988
7. BB Lohray VB Lohray AC Bajji S Kalchar RR Poondra S Padakanti R Chakrabarti RK Vikramadithyan P Misra S Juluri NVSR Mamidi R Rajagopalan 2001 (-)3-[4-[2-(Phenoxazin-10-yl)ethoxy]phenyl]-2-ethoxypropanoic acid [(-)DRF 2725]: a dual PPAR α/γ agonist with potent antihyperglycemic and lipid modulating activity J Med Chem 44 2675 2678
8. Potlapally RK, Siripragada MR, Kotra NM, Sirisilla R, Mamillapalli RS, Gaddam OR (2002) WO 02/24625, assigned to Dr. Reddy's Research Foundation
9. T Sasaki I Otsuka 1917 The stereochemistry of the bacterial decomposition of albumin J Biol Chem 32 533 538
10. P Sauerberg I Pettersson L Jeppesen PS Bury JP Mogensen K Wassermann CL Brand J Sturis HF Woldike J Fleckner AST Andersen SB Mortensen LA Svensson HB Rasmussen SB Lehmann Z Polivka K Sindelar V Panajotova L Ynddal EM Wulff 2002 Novel tricyclic-α-alkyloxyphenylpropionic acids: dual PPAR α/γ agonists with hypolipidemic and antidiabetic activity J Med Chem 45 789 804
11. M Takamura H Yanagisawa M Kanai M Shibasaki 2002 Efficient synthesis of antihyperglycemic (S)-α-aryloxy-β-phenylpropionic acid using a bifuctional asymmetric catalyst Chem Pharm Bull 50 1118 1121
12. N Valls M Lopez-Canet M Vallribera J Bonjoch 2001 First total syntheses of Aeruginosin 298-A and Aeruginosin 298-B, based on a stereocontrolled route to the new amino acid 6-hydroxyoctahydroindole-2-carboxylic acid Chem Eur J 7 3446 3460
13. N Valls M Vallribera M Lopez-Canet J Bonjoch 2002 Synthesis of Microcin SF608 J Org Chem 67 4945 4950
14. HQ Wang QL Zeng H Fang YF Zhao 2005 (S)-3-[4-(Benzyloxy)phenyl]-2- hydroxypropanoic acid Acta Crystallogr E 61 o2286 o2297
15. Z Wang B La JM Fortunak XJ Meng GW Kabalka 1998 Enantioselective synthesis of α-hydroxy carboxylic acids: direct conversion of α-oxocarboxylic acids to enantiomerically enriched α-hydroxy carboxylic acids via neighboring group control Tetrahedron Lett 39 5501 5504
16. W Weng QH Wang BX Yao QL Zeng 2004 Enantioseparation of amino acid derivatives on an immobilized network polymer derived from L-tartaric acid J Chromatogr A 1042 81 87
17. 8-MonoPhos Tetrahedron: Asymmetry 13 115 117
18. 8-MonoPhos and its application in catalytic enantioselective hydrogenation of α-dehydroamino acids Tetrahedron 58 8799 8803
19. Q Zeng Z Liu B Li F Wang 2004 Mild and effective N-phthaloylation of amino acids Amino Acids 27 183 186
20. QL Zeng HQ Wang TJ Wang YM Cai W Weng YF Zhao 2005a Vanadium-catalyzed enantioselective sulfoxidation and concomitant, highly efficient kinetic resolution provide high enantioselectivity and acceptable yields of sulfoxides Adv Synth Catal 347 1933 1936
21. QL Zeng HQ Wang W Weng WS Lin YX Gao XT Huang YF Zhao 2005b Substituent effects and mechanism elucidation of enantioselective sulfoxidation catalyzed by vanadium Schiff base complexes New J Chem 29 1125 1127