Preparation of a chiral synthon for an HBV inhibitor: enzymatic asymmetric hydrolysis of (1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol diacetate and enzymatic asymmetric acetylation of (1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol

Autor:	Jing Liang, Yadagiri Pendri, Ramesh N. Patel, Amit Banerjee, Chung-Pin Chen, Richard H. Mueller
Rok vydání:	2006
Předmět:	biology Stereochemistry Organic Chemistry Diol Enantioselective synthesis Catalysis Inorganic Chemistry Acylation Isopropenyl acetate chemistry.chemical_compound Hydrolysis chemistry biology.protein Physical and Theoretical Chemistry Lipase Enantiomeric excess Ene reaction
Zdroj:	Tetrahedron: Asymmetry. 17:175-178
ISSN:	0957-4166
Popis:	Enantioselective asymmetric hydrolysis of (1α,2β,3α)-2-(benzyloxymethyl)-cyclopent-4-ene-1,3-diol diacetate 1 to the corresponding (+)-monoacetate 2 was carried out using lipase PS-30 from Pseudomonas cepacia or pancreatin. A reaction yield of 85 M % with an enantiomeric excess (ee) of 98% was obtained. Using pancreatin, a reaction yield of 75 M % with an ee of 98.5% was obtained. Asymmetric acetylation of (1α,2β,3α)-2-(benzyloxymethyl)-cyclopent-4-ene-1,3-diol 3 to the corresponding (−)-monoacetate 4 was carried out using lipase PS-30 with isopropenyl acetate as the acylating agent. A reaction yield of 80 M % with an ee of 98% was obtained for (−)-monoacetate 4 .
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::0bd18c9b269094b066d692acd2a8a0b5 https://doi.org/10.1016/j.tetasy.2005.08.061 Zobrazit plný text záznamu Full Text from ScienceDirect