新产品编号:2020723

Chemical Name: (16alpha,17beta)-3,17-Dihydroxyestra-1(10),2,4-triene-16-carboxylic acid 2-fluoroethyl ester
项目整合开发状态: Preclinical
项目研究机构: Yale University (Originator)
合成路线:Claisen condensation of 3-O-benzylestrone (I) with ethyl formate in the presence of NaH afforded the 16-hydroxymethylene derivative (II),which was further converted to enol ether (III) by alkylation with ethyl iodide.Stereoselective ketone reduction of (III) with LiAlH4 gave the 17-beta alcohol (IV),which was esterified with Ac2O in pyridine to provide acetate (V).Acid hydrolysis of the enol ether of (V) produced the 16-alpha aldehyde (VI),and subsequent Jones oxidation furnished the carboxylic acid (VII).After basic hydrolysis of the acetate ester of (VII) to yield (VIII),its O-benzyl protecting group was removed by hydrogenolysis over Pd/C,yielding diol (IX).Finally,Fischer esterification with 2-fluoroethanol in the presence of p-toluenesulfonic acid gave rise to the title fluoroethyl ester.