85359-12-2

Upstream product

• 15001-40-8 4-amino-3-benzyloxy-1,3,5⁽¹⁰⁾-estatrien-17-one 
• 3131-23-5 4-hydroxyestrone 
• 100-44-7 benzyl chloride 
• 360771-94-4 3-benzyloxy-4-hydroxy-17,17-ethylenedioxy-1,3,5⁽¹⁰⁾-estratrien-6-one acetate 
• 360771-93-3 3-benzyloxy-4-hydroxy-17,17-ethylenedioxy-1,3,5⁽¹⁰⁾-estratrien-6-one 
• 360771-91-1 3,4-dihydroxy-17,17-ethylenedioxy-1,3,5⁽¹⁰⁾-estratrien-6-one diacetate 
• 360771-92-2 3,4-dihydroxy-17,17-ethylenedioxy-1,3,5⁽¹⁰⁾-estratrien-6-one 
• 360771-95-5 3-benzyloxy-17,17-ethylenedioxy-1,3,5⁽¹⁰⁾-estratrien-4-ol 

Downstream Products

• 85359-13-3 sodium 3-benzyloxy-4-hydroxy-1,3,5⁽¹⁰⁾-estatrien-17-one 4-sulfate 
• 88016-83-5 3-benzyloxy-4-methoxy-1,3,5⁽¹⁰⁾-estratrien-17-one 
• 85359-18-8 sodium 4-hydroxy-3-methoxy-1,3,5(10)-estatrien-17-one 4-sulfate 
• 85359-14-4 sodium 3,4-dihydroxy-1,3,5(10)-estatrien-17-one 4-sulfate 
• 58562-33-7 4-methoxyestrone 

Relevant academic research and scientific papers

Selective synthesis of 4-methoxyestrogen from 4-hydroxyestrogen

The introduction of an oxygen atom into the C-6 position of 4-hydroxyestrogen allowed for the selective methylation of the two phenolic hydroxyl groups. When the 6-oxo derivative of 4-hydroxyestrone was benzylated in ethanol, only the 3-monobenzyl ether was obtained without formation of the 4-monobenzyl ether. Moreover, the 6-carbonyl group was further reduced to methylene almost quantitatively in the reaction of 4-acetoxy-6-oxoestrone 3-benzyl ether derivative with sodium borohydride. Therefore, 4-methoxyestrogen was synthesized by essentially combining these two reactions. Copyright

Methylation of catechol estrogen with diazomethane

Dynamic aspects of methylation of catechol estrogen with diazomethane were investigated by means of thin-layer chromatography. The methylation rate of the hydroxyl group at the C-3 position was almost the same as that of the C-2 hydroxyl group in the reaction of 2-hydroxyestrogen, and 2-3 times that of the C-4 hydroxyl group in the reaction of 4-hydroxyestrogen. In these experiments, the maximum yields of 2-methoxyestrone, 2-hydroxyestrone 3-methyl ether, 4-methoxyesterone and 4-hydroxyesterone 3-methyl ether were 32, 39, 13, and 70%, respectively. In addition, demethylation of catechol estrogen dimethyl ethers with boron tribromide and synthesis of 4-hydroxyestrone monomethyl ethers are described.