Baker's yeast reduction of PEG-linked acetoacetate

被引:6
作者
Bonora, GM [1 ]
Drioli, S [1 ]
Forzato, C [1 ]
Nitti, P [1 ]
Pitacco, G [1 ]
机构
[1] Univ Trieste, Dipartimento Sci Chim, I-34127 Trieste, Italy
关键词
Baker's yeast; bioreduction; organic solvent; PEG;
D O I
10.2174/1570178053400135
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Bioreduction of PEG-acetoacetate 1 is achieved using dry baker's yeast in toluene with a small amount of added water. After detachment from the polymer under basic conditions, the corresponding (S)-(+)-3-hydroxybutanoic acid 3 was esterified with Me3SiCl and ethanol and ethyl (S)-(+)-3-hydroxybutanoate 4 was isolated with 97% e.e. and 70% overall yield.
引用
收藏
页码:89 / 91
页数:3
相关论文
共 23 条
[1]   Synthesis of new poly(ethyleneglycol)s with a high loading capacity [J].
Benaglia, M ;
Annunziata, R ;
Cinquini, M ;
Cozzi, F ;
Ressel, S .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (24) :8628-8629
[2]  
BROOK MA, 1983, SYNTHESIS-STUTTGART, P201
[3]  
Brown RCD, 1998, J CHEM SOC PERK T 1, P3293
[4]  
Chandrasekhar S, 1999, SYNLETT, P1061
[5]   BAKERS-YEAST MEDIATED TRANSFORMATIONS IN ORGANIC-CHEMISTRY [J].
CSUK, R ;
GLANZER, BI .
CHEMICAL REVIEWS, 1991, 91 (01) :49-97
[6]  
CSUK R, 2000, STEREOSELECTIVE BIOC, pCH19
[7]   Chemoenzymatic polymer-supported liquid phase synthesis of glucose γ-aminobutyric ester [J].
de Torres, C ;
Fernández-Mayoralas, A .
TETRAHEDRON LETTERS, 2003, 44 (11) :2383-2385
[8]  
Faber K., 2004, BIOTRANSFORMATION OR
[9]   TRANS-ESTERIFICATION OF 3-OXO ESTERS WITH ALLYLIC ALCOHOLS [J].
GILBERT, JC ;
KELLY, TA .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (02) :449-450
[10]   Organic synthesis on soluble polymer supports: Liquid-phase methodologies [J].
Gravert, DJ ;
Janda, KD .
CHEMICAL REVIEWS, 1997, 97 (02) :489-509