78479-31-9

Upstream product

• 72-33-3 mestranol 
• 115464-37-4 3-methoxy-17α(Z-2-tributylstannylvinyl)-1,3,5(10)-estratrien-17β-ol 
• 94887-68-0 (17α,20E)-21-(tributylstannyl)-19-norpregna-1,3,5(10),20-tetraene-3,17-diol 3-(methyl ester) 
• 81844-94-2 ((17α,20E)-17-hydroxy-3-methoxy-19-norpregna-1,3,5(10),20-tetraen-21-yl)boronic acid 

Downstream Products

• 17550-03-7 (9S,13S,14S,17S)-17-ethyl-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol 

Relevant academic research and scientific papers

Synthesis, receptor binding, and tissue distribution of (17α,20E)- and (17α,20Z)-21-[125I]Iodo-19-norpregna-1,3,5(10),20-tetraene-3,17-d ol

The isomeric (17α,20E)- and (17α,20Z)-(iodovinyl)estradiol derivatives 3 and 6, and their no-carrier-added (nca) [125I]iodovinyl analogues, were tested for their relative target tissue retention and binding affinity for the estrogen receptor. The (iodovinyl)estradiols 3 and 6 were prepared via destannylation of the (17α,20E)- and (17α,20Z)-tributylstannyl precursors 2 and 4 with retention of configuration. Selective formation of the E or Z isomers 2 and 4 during the reaction of 17α-ethynylestradiol 1a with tri-n-butyltin hydride was controlled by the presence or absence of the catalyst, the polarity of the solvent, and the reaction temperature. The nca [125I]iodovinyl analogues [125I]-3a and [125I]-6a were obtained in good radiochemical yield and high purity by treatment of 2a and 4a with [125I]NaI in the presence of H2O2 and chloroamine-T, respectively. Of the two isomeric iodovinyl derivatives 3 and 6, the 20Z isomer 6a exhibited the highest receptor binding affinity and the [125I]-6a gave the highest in vivo receptor-mediated target tissue uptake.

Synthesis of 17α-(Iodovinyl)estradiol and analogous derivatives by iododestannylation of insoluble polymer-supported organotin precursors

Iodoestrogen derivatives were prepared by iododestannylation of insoluble polymer-supported organotin precursors.

Estrogenic 17α-halogen-vinylestranes

17α-bromo-α and 17α-iodo-vinyl-estrane derivatives of general formula I STR1 wherein X is a bromine or iodine atom in Z or E position, R1 is hydrogen, hydroxy or acyloxy with up to 3 C atoms, R2 is hydrogen, alkyl with up to 3 C atom

Synthesis and evaluation of (17 alpha,20E)-21-[125I]iodo-19-norpregna-1,3,5(10),20-tetraene-3,17 -diol and (17 alpha,20E)-21-[125I]iodo-11 beta-methoxy-19-norpregna-1,3,5(10),20-tetraene-3,17-diol (17 alpha-(iodovinyl)estradiol derivatives) as high specific activity potential radiopharmaceuticals.

Two 17 alpha-[125I]iodovinyl estradiol derivatives 4b,d possessing high specific activity have been prepared and tested as potential radiopharmaceuticals. The use of the 3-acetyl derivatives 2c,e and the replacement of iodine monochloride with sodium iodide and Chloramine-T in THF/phosphate buffer (pH 7.0) permitted us to synthesize no-carrier-added (17 alpha,20E)-21-[125I]iodo-19-norpregna-1,3,5(10),20-tetraene-3,17-d iol (4b) and (17 alpha,20E)-21-[125I]iodo-11 beta-methoxy-19-norpregna-1,3,5(10),20-tetraene-3,17-diol (4d) with 50% radiochemical yield and high purity. Although the specific activity represents only half of the theoretical value in some cases, this modified approach is a substantial improvement over the previously published method. Our preliminary distribution studies indicate that although both 4b and 4d localize in the tissues known to have a large concentration of estrogen receptors, 4d accumulates in higher amounts in target tissues and provides a high target to nontarget ratio.

1,3,2-BENZODIOXABOROLE IN ORGANIC SYNTHESIS: PREPARATION OF VINYL IODIDES

1,3,2-Benzodioxaborole readily hydroborates alkynes to form vinylboronic esters.The esters can be hydrolyzed to the corresponding vinylboronic acids which react with sodium iodide and chloramine-T to form isometrically pure (E)-iodoalkenes.