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Preparation of all trans ‐retinoic‐11‐ 3 H acid and all trans ‐retinyl‐11‐ 3 H acetate
Author(s) -
Kaegi Hans H.,
Degraw Joseph I.
Publication year - 1981
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580180803
Subject(s) - chemistry , saponification , diazomethane , retinoic acid , aldehyde , lithium (medication) , alcohol , retinyl acetate , acetylation , lithium aluminium hydride , medicinal chemistry , organic chemistry , biochemistry , medicine , gene , endocrinology , catalysis
Trans ‐ionylidineacetaldehyde‐1‐ 3 H ( 3 ) was obtained by reduction of unlabeled aldehyde ( 1 ) with lithium borotritide, followed by reoxidation of the tritio alcohol ( 2 ). Condensation of aldehyde ( 3 ) with triethyl 3‐methyl‐4‐phosphonocrotonate ( 7 ), followed by saponification of the retinoic ethyl ester ( 8 ), afforded trans ‐retinoic‐11‐ 3 H acid ( 9 ). Esterification of the crystalline acid with diazomethane, and subsequent reduction of the methyl trans ‐retinoate‐11‐ 3 H with lithium aluminum hydride, yielded trans ‐retinol‐11‐ 3 H, which was acetylated in situ to give trans ‐retinyl‐11‐ 3 H acetate ( 10 ).