http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-1508196-A

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classificationCPCInventive http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07F9-5428
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filingDate 1975-08-20-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 1978-04-19-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber GB-1508196-A
titleOfInvention (3r,3'r)-15,15'-didehydrozeaxanthin
abstract 1508196 Didehydrozeaxanthin F HOFFMANN-LA ROCHE & CO AG 20 Aug 1975 [1 Nov 1974] 47892/76 Divided out of 1508195 Heading C2C The invention comprises [3R,3<SP>1</SP>R]-15,15<SP>1</SP>- didehydro-zeaxanthin. The compound may be prepared by reacting [4R,6R]-4-hydroxy-2,2,6- trimethylcyclohexanone with but-3-yn-2-ol suitably after the free hydroxy group has been masked by treatment of the ketone with isopropenyl methyl ether to yield 2-hydroxy-4- {[4R,6R] - 1,4 - dihydroxy - 2,2,6 - trimethylcyclohex - 1 - yl} but - 3 - yne, acetylating this to give 2 - acetoxy - 4 - {[4R,6R] - 4 - acetoxy- 1 - hydroxy - 2,2,6 - trimethyl - cyclohex - 1 - yl} - but-3-yne, dehydrating this to give the cyclohexene derivative and hydrogenating to yield [3R]-3-hydroxy-#-ionol. The ionol may be converted to a 4-{[4R]-4-hydroxy-2,2,6-trimethyl - cyclohex - 1 - en - 1 - yl} but - 3 - ene- 2-triarylphosphonium halide which may be condensed with 4,9-dimethyl-dodeca-2,4,8,10-tetraen-6-yne-1,12-dial to give the required didehydro zeaxanthin. Alternatively the ionol may be oxidized to [3R]-3-hydroxy-#-ionone, which is then reacted with sodium acetylide to give [3R] - 3 - hydroxy - ethynyl - # - ionol, subsequently hydrogenated to [3R] - 3 - hydroxy - vinyl - # - ionol, converted to [3R]- 3-hydroxy-#-ionylidene ethyl triphenyl phosphonium chloride or bromide which is then condensed with 2,7-dimethyl octa-2,6-then-4- yne-1,8-dial to give the required didehydrozeaxanthin.
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priorityDate 1974-11-01-04:00^^<http://www.w3.org/2001/XMLSchema#date>
type http://data.epo.org/linked-data/def/patent/Publication

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