PRODUCTION OF Z-CYCLOHEXYLIDENEACETIC ACID DERIVATIVE
PURPOSE:To obtain the subject compound which is a synthetic intermediate for 1alpha-hydroxyvitamin D derivatives in high selectivity in a short process by reacting a readily available cyclohexanone derivative with a silylacetic acid ester as raw materials in the presence of a base. CONSTITUTION:A cy...
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Zusammenfassung: | PURPOSE:To obtain the subject compound which is a synthetic intermediate for 1alpha-hydroxyvitamin D derivatives in high selectivity in a short process by reacting a readily available cyclohexanone derivative with a silylacetic acid ester as raw materials in the presence of a base. CONSTITUTION:A cyclohexanone derivative of formula I (R to R are H or protecting group of OH; A is H, OH or protected OH) obtained from inexpensive mannitol or tartaric acid is made to react with a silylacetic acid ester of formula II (R is alkyl; R to R are alkyl or aryl) in the presence of a base (e.g. lithium hexamethyl disilazide) to afford the objective Z-cyclohexylideneacetic acid derivative of formula III, e.g. ethyl 2-(1-ethoxyethoxy) methyl-3,4-(dimethylmethylendioxy)-5-(methoxymethoxy)cyclohexylideneac etate. |
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