Lipase-catalyzed monoprotection of 1,4-diols in an organic solvent using vinyl benzoate as acyl transfer agent

Tetrahedron Letters

Volumn 44, Issue 18, 2003, Pages 3663-3665

  Ciuffreda, Pierangela ^a   Casati, Silvana ^a   Santaniello, Enzo ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; BENZOIC ACID; ORGANIC SOLVENT; TERT BUTYL METHYL ETHER; TRIACYLGLYCEROL LIPASE; VINYL DERIVATIVE;

ARTICLE; BACTERIUM; CATALYSIS; CHEMICAL REACTION; ENZYME ACTIVITY; MONOBENZOYLATION; MUCOR MIEHEI; PROTECTION; STEREOCHEMISTRY;

MUCOR; RHIZOMUCOR MIEHEI;

EID: 0037471464     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00694-4     Document Type: Article

References (16)

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11. Porcine pancreatic lipase (24 U/mg solid) was purchased from Fluka. Lipase from Pseudomonas sp. (Lipase PS 'Amano', 30 U/mg solid) and from Candida cylindracea (Lipase AYS 'Amano', 31.6 U/mg solid) were purchased from Amano Pharmaceutical. Candida antarctica lipase (Novozym 435®, acrylic resin supported lipase, 11.4 U/mg solid) was purchased from Novo Nordisk Bioindustrial Group. Lipase from Mucor miehei (Chirazyme® L-9,c.-f., C2, lyo, carrier-fixed lipase, 8 U/mg solid) was purchased from Roche Molecular Biochemicals.
12. When the reaction was carried out at 0°C, longer reaction time was required but regioselectivity was not enhanced.
13. Butane-1,4-diol ( 1a ) and (Z)-2-butene-1,4-diol ( 2a ) were commercially available (Fluka); (E)-1,2-cyclopropanedimethanol ( 4a ) was purchased from Aldrich. (E)-2-butene-1,4-diol ( 3a ) was prepared by reduction of diethyl fumarate, according to: Corlay H., Motherwell W.B., Pennell A.M.K., Shipman M., Slawin A.M.Z., Williams D.J., Binger P., Stepp M. Tetrahedron. 13:1996;4883-4902.
14. 3) δ 8.03 (2H, d, J=7.7, o-Ph H), 7.53 (1H, dd, J=7.7 and 7.7 Hz, p-Ph H), 7.42 (2H, dd, J=7.7 and 7.7 Hz, m-Ph H), 4.21 (1H, dd, J=6.3 and 11.2 Hz, CHHOBz), 4.16 (1H, dd, J=7.0 and 11.2 Hz, CHHOBz), 3.53 (1H, dd, J=6.3 and 11.2 Hz, CHHOH), 3.46 (1H, dd, J=7.0 and 11.2 Hz, CHHOH), 1.18 (2H, m, cyPr CH), 0.64 (1H, ddd, J=4.9, 4.9 and 8.4 Hz, cyPr CHH), and 0.59 (1H, ddd, J=4.9, 4.9 and 8.4 Hz, cyPr CHH).
15. Ferraboschi P., Grisenti P., Manzocchi A., Santaniello E. Tetrahedron: Asymmetry. 5:1994;691-698.
16. 2OH).