Method for producing optically active glycol derivatives

Details Method for producing optically active glycol derivatives Method for producing optically active glycol derivatives

1986-04-01

1988-05-17

Rosen, Sam

Chemistry: molecular biology and microbiology

Process of utilizing an enzyme or micro-organism to destroy...

Resolution of optical isomers or purification of organic...

435130, C07P 4100

Patent

active

047450665

ABSTRACT:
A method for producing optically active glycol derivatives by biochemical resolution which comprises contacting a racemic ester of the general formula 1 ##STR1## (wherein R.sub.1 is an aliphatic hydrocarbon group of 1 to 16 carbon atoms, R.sub.2 is an aliphatic hydrocarbon group of 1 to 8 carbon atoms, and R.sub.3 is an aromatic hydrocarbon group such as phenyl, tolyl or naphtyl) with a microorganism- or animal organ-derived enzyme having stereoselective hydrolytic activity to asymmetrically hydrolyze said racemic ester of general formula 1 to produce an optically active alcohol of general formula 2* ##STR2## (wherein R.sub.1 and R.sub.3 have the same meanings as defined above) and an unreacted ester of the general formula 1* ##STR3## (wherein R.sub.1, R.sub.2 and R.sub.3 have the same meanings as defined hereinbefore), separating the optically active compounds from each other, hydrolyzing said ester of general formula 1* to give an optically active glycol derivative which is antipodal to the alcohol of general formula 2* and, then, isolating the same optically active glycol derivative. The invention provides a method for producing optically active glycol derivatives, which is expedient, does not require costly reagents and is suited to commercial scale production.

REFERENCES:
patent: 4601987 (1986-07-01), Klibanov et al.
S. Iriuchijima and N. Kojima, "Asymmetric Hydrolysis of (.+-.)-1,2-Diacetoxy-3-chloropropane and Its Related Compounds with Lipase, Synthesis of Optically Pure (S)-Propranolol," Agric. Biol. Chem., 1982.
S. Iriuchijima, A. Keiyu and N. Kojima, "Asymmetric Hydrolysis of (.+-.)-1-Acetoxy-2,3-dichloropropane with Enzymes and Microorganisms", Agric. Biol. Chem., 1982.

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