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AssigneeNone recorded
InventorsRobert Antony Holt, Stuart Richard Rigby, David Waterson
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Optically active 2-substituted tetrahydropyran-4-ols or esters thereof may be prepared using esterases or hydrolases from the corresponding racemic mixtures of esters or alcohols. This provides a route to the corresponding optically active ketones. The racemic mixtures are preferably in the cis-form. such mixtures may be produced by reacting but-3-ene-1-ol with an aldehyde in the presence of an acid.
A process of producing an optically active cis 2-substituted tetrahydropyran-4-ol which comprises stereospecifically hydrolysing an ester thereof with a stereospecific hydrolase.
Dependencies are inferred from the claim text.
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No related US applications are recorded in the indexed filing history.
With aromatic rings attached in position 2 only: not hydrogenated in the hetero ring, e.g. flavones
Oxygen as only ring hetero atoms: containing a six-membered hetero ring, e.g. fluorescein
By ester formation, lactone formation or the inverse reactions: by esterification of alcohol- or thiol groups in the enantiomers or the inverse…
Heterocyclic compounds
Term ended 26 May 2018 (estimated)
USPTO file history isn’t available for this patent, so only indexed dates are shown.
THIS INVENTION relates to a Process for the Production of Optically Active 2-Substituted tetrahydropyran-4-ones.
Certain tetrahydropyran-4-ones are of interest as chemical intermediates in the production of biologically active materials, for example those of European Patents 465,812; 462,813; 409,413; 420,511; 410,661; 385,662 and 375,404. In at least some cases compounds of enhanced activity are produced if the tetrahydropyran-4-one is 2-substituted and is in the (S) configuration. Compounds of the (R) configuration are of possible research interest.
This invention comprises a process of producing an optically active 2-substituted tetrahydropyran-4-ol or ester thereof which comprises stereospecifically esterifying a 2-substituted tetrahydropyran-4-ol using a stereospecific esterase or stereospecifically hydrolysing an ester thereof with a stereospecific hydrolase.
Preparation of Racemic Cis-2-Methyltetrahydro-(4H)-Pyran-4-ol Butyrate Ester
Racemic cis-2-methyltetrahydro-(4H)-pyran-4-ol was prepared by the method of E Hanschke (Chemische Berichte (1955), volume 88, p 1053).
Typically esterification was carried out as follows.