ISSN:
0170-2041
Schlagwort(e):
Porcine pancreas lipase
;
1,3-Dioxane-5-carboxylic acid
;
Saponification, enantioselective
;
Chemistry
;
Organic Chemistry
Quelle:
Wiley InterScience Backfile Collection 1832-2000
Thema:
Chemie und Pharmazie
Notizen:
Enantioselective Saponification of Substituted, Achiral 3-Acyloxy-propionates with Lipases: Synthesis of Chiral Derivatives of „Tris(hydroxymethyl)methane“Ethyl 3-hydroxy-2-(hydroxymethyl)propionate (11) was synthesized with an overall yield of 40% starting from the pentaerythritol derivative 5,5-bis(hydroxymethyl)-1,3-dioxane (7). Both OH groups of 11 were acylated (ethanoyl-, propanoyl-, butanoyl, hexanoyl, and octanoyl derivatives 6a - e), and the formed triesters were partially hydrolyzed by lipases. According to 19F-NMR analysis of the corresponding Mosher ersters, the monocapronate 12d formed by PPL (porcine pancreas lipase) showed an enantiomeric ratio of 93.5:6.5 (87% ee). Using standard reactions, it was converted into chiral non-racemic derivatives 16 (O-benzyl-O′-silyl) and 21 (O-benzyl-O′-methoxymethyl) of the C3v-symmetric title compound. Possible applications of these derivatives are discussed. A “model” for the enantioselectivity of PPL hydrolysis is formulated.
Zusätzliches Material:
4 Tab.
Materialart:
Digitale Medien
URL:
http://dx.doi.org/10.1002/jlac.199019900172
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