Process for the preparation of meso-zeaxanthin
AssigneeBASF SE
InventorsHansgeorg Ernst, Klaus Henrich, Klaus Ditrich
Life of this patent
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Abstract
A process for the preparation of optically pure acetylenediols of the formulae R-I and S-I 1 and their further reaction to give meso-zeaxanthin are described.
Claims22
A process for the preparation of meso-zeaxanthin,
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- which comprises
- a) resolving a racemic mixture of the acetylenediols R-I and S-I
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- into its antipodes,
- b) converting the separated antipodes R-I and S-I in each case into the C15-phosphonium salts R-II and S-II respectively
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- in which Ph is aryl and X is an anion equivalent of an inorganic or organic acid,
- c) reacting the phosphonium salts R-II or S-II with a C10-dial monoacetal of the general formula III,
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- in which the substituents R1 and R2 independently of one another are C1-C8-alkyl or, together with the oxygen atoms and the carbon atom to which they are bonded, can form a 1,3-dioxolane or 1,3-dioxane ring of the following structures
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- in which R3 and R4 and also R5 in each case independently of one another can be hydrogen or C1-C4-alkyl, in a Wittig reaction to give the C25-acetals R-IV or S-IV,
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- d) converting the C25-acetals R-IV or S-IV into the C25-aldehydes R-V or S-V
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- e) and reacting the C2-5-aldehyde R-V with the C15-phosphonium salt S-II or the C25-aldehyde S-V with the C15-phosphonium salt R-II in a Wittig reaction to give sterically uniform meso-zeaxanthin.
A process for the preparation of optically pure acetylenediols of the formulae R-I and S-I,
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- which comprises converting a racemic mixture of the acetylenediols R-I and S-I into a diastereomer mixture using an optically active auxiliary reagent, separating the diastereomers and then removing the auxiliary reagent again.
An optically active cyclohexane derivative of the general formula or R-VI or S-VI,
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- in which the substituent R6 is an optically active urethane radical, carbonate radical, sulfonate radical or an acyl radical.
A 2,4-dichlorophenoxypropionic acid ester of the formula R-VIa or S-VIa, or R-VIb or S-VIb
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An optically active acetylenediol of the formula S-I
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An optically active acetylene compound of the general formula S-VII,
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- in which the substituents independently of one another have the following meaning:
- R7 is hydrogen, C1-C12-acyl or a hydrolytically cleavable acetal or ether protective group;
- R8 is hydrogen or C(CH3)OR9—CH═CH2;
- R9 is lithium or hydrogen.
An optically active cyclohexane derivative of the general formula S-XI,
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- in which R10 is a nonchiral C1-C12-acyl radical or a hydrolytically cleavable acetal or ether protective group.
Dependencies are inferred from the claim text.