Lipozyme-mediated regioselective esterification of isosorbide under solvent-free conditions

Synthetic Communications

Volumn 27, Issue 22, 1997, Pages 3847-3852

  Chalecki, Zbigniew ^a   Guibé Jampel, Eryka ^b  

^a WARSAW UNIVERSITY OF TECHNOLOGY   (Poland)

^b UNIVERSITÉ PARIS SUD   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ENZYME; ISOSORBIDE;

CATALYSIS; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REVIEW; STEREOCHEMISTRY;

EID: 1842404133     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919708005907     Document Type: Review

References (15)

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2. Loupy, A. and Monteux, D. Tetrahedron Lett., 1996, 37, 7023.
3. Ropuszynski, S.; Jasinski, W. and Perka, J. Przemysl Chemiczny, 1970, 49, 222.
4. Stoss, P.; Merrath, P. and Schlüter, G. Synthesis, 1987, 174.
5. Cekovic, Z. and Tokic, Z. Synthesis, 1989, 610 and references there in.
6. Seemayer, R.; Bar, N. and Schneider, M.P. Tetrahedron: Asymmetry, 1992, 3, 1123.
7. Hiratake, J.; Inagaki, M.; Nishioka, T. and Oda, J. J. Org. Chem., 1988, 53, 6130.
8. Novozym and Lipozyme were a gift from Novo Nordisk.
9. Guibé-Jampel, E. and Rousseau, G. Tetrahedron Lett., 1987, 28, 3563.
10. Godtfredsen, S.E.; Ingvorsen, K.; Eigtved, P. and Hansen, T.T. "Materials for 4th European Congress on Biotechnology" 1987, pp. 14-19.
11. Table 2: GC Retention times (min) of esters of isosorbide. Products a b c d e 4(exo) 9.15 11.15 13.56 14.66 16.23 3(endo) 9.77 11.73 14.14 15.16 16.68 5(di) 15.64 18.71 24.66 38.12 51.05 GC analyses were performed on a Fisons Instruments GC 8000 series chromatograph with flame ionization and capillary column OV 1 12m, ID 0.22 mm, ef 0.1 μm, (carrier gas He at 70kPa) with the same gradient for the products a, b, c, d: 100°C to 270°C (10°C/min) then 270°C. For the products e the conditions were: 100°C to 280°C (10°C/min) then 280°C during 35 min. The retention time of isosorbide was 2,43 min. Internal standard for calibration in GC was methyl myristate.
12. 2); 3,72-3,83 (1H, q, H6a); 3,85-3,98 (3H, m, H1a, 1b, 6b); 4,3-4,38 (1H, broad, H2); 4,38-4,45 (1H, d, H3); 4,82-4,9 (1H, t, H4); 5,12-5,22 (1H, q, H5).
13. Mass analyses were performed on NERMAG R10-10 equipped with CPSil-5, 25m capillary column.
14. Gelo-Pujic, M.; Guibé-Jampel, E.; Loupy, A.; Galema, S.A. and Mathé, D. J. Chem. Soc., Perkin Trans. 1, 1996, 2777-2780.
15. Carrillo-Munoz, J.-R.; Bouvet, D.; Guibé-Jampel, E.; Loupy, A. and Petit, A. J. Org. Chem., 1996, 61, 7746-7749.