Process for preparing (R) and (S)-1,2-isopropylideneglycerol by

Details Process for preparing (R) and (S)-1,2-isopropylideneglycerol by Process for preparing (R) and (S)-1,2-isopropylideneglycerol by

1993-02-12

1994-07-26

Robinson, Douglas W.

Chemistry: molecular biology and microbiology

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

Resolution of optical isomers or purification of organic...

23296, C12P 4100

Patent

active

053326741

ABSTRACT:
A process is described for separating the optical isomers of 1,2-isopropylideneglycerol, of formula (I), comprising partially stereoselective enzymatic hydrolysis of 1,2-isopropylideneglycerol benzoyl ester (II) catalyzed by a free or immobilized lipase, the hydrolysis being conducted in the presence of a cosolvent and followed by crystallization enabling crystals of (II) in raceme form and mother liquor containing (II) in the form of the pure enantiomer to be selectively obtained.
The compound (I) is widely used industrially as an intermediate in the synthesis of chiral drugs such as (R)-(-)-carnitine, (S)-beta-blockers, (S)-antiviral agents, analgesic drugs etc.

REFERENCES:
patent: 4957868 (1990-09-01), Yushina et al.
Chemical Abstracts, AN-57587m, vol. 111, No. 7, Aug. 14, 1989, F. Aragozz, et al., "Enantioselective Microbial Reduction of Monoesters of 1,3-Dihydroxypropanone: Synthesis of (S)-And (R)-1,2-O=Isopropylideneglycerol".
Chemical Abstracts, AN-181855y, vol. 114, No. 19, May 13, 1991, F. Aragozzini, et al., "Enantioselective Hydrolysis of Benzoyl 1,2-O-Isopropylideneglycerol by Bacillus Coagulans".

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