22845-55-2

Upstream product

• 554-10-9 3-iodo-propane-1,2-diol 
• 5879-91-4 4-(cis-6-methoxy-2-phenyltetralin-1-yl)phenol 
• 96-24-2 3-monochloro-1,2-propanediol 
• 1729-38-0 1-(p-hydroxyphenyl)-6-methoxy-2-phenyl-3,4-dihydronaphthalene 

Relevant academic research and scientific papers

An ortho-quinodimethane route to Lasofoxifene and U23469

Lasofoxifene, a third-generation selective estrogen receptor modulator, could be synthesized via regio-and stereoselective [4 + 2] cycloaddition between an ortho-quinodimethane and a borylalkene. This protocol was also applicable to the synthesis of antie

Antiestrogens and antiestrogen metabolites: Preparation of tritium-labeled (±)-cis-3-[p-(1,2,3,4-tetrahydro-6-methoxy-2-phenyl-1-naphthyl)phenoxy]-1,2-propanediol (U-23469) and characterization and synthesis of a biologically important metabolite

The Upjohn antiestrogen (±)-cis-3-[p-(1,2,3,4-tetrahydro-6-methoxy-2-phenyl-1-naphthyl)phenoxy]-1,2-propanediol (2b, U 23469) has been prepared in tritium-labeled form by reduction of an unsaturated dihydronaphthalene precursor with carrier-free tritium gas over a palladium catalyst followed by alkylation with 3-iodo-1,2-propanediol. After extensive chromatographic purification, the final material was obtained with a specific activity of 13 Ci/mmol and a radiochemical purity of 94%. In vivo studies with immature rats show that [3H]2b is slowly converted to a more polar metabolite that is selectively accumulated in the nuclear fraction of the uterus where it is bound to the estrogen receptor. Chromatographic comparisons indicate that this metabolite is a demethylated analogue, a compound that has an affinity for estrogen receptor more than 300 times greater than that of 2b. These studies suggest that the demethylated analogue may be a biologically important metabolite of 2b that is involved in the action of this antiestrogen.