3434-76-2

Usage

Uses

Used in Pharmaceutical Industry:
3-O-Methyl 17α-Estradiol is used as a pharmaceutical compound for its antioxidant properties. It can be employed in the development of drugs targeting conditions where oxidative stress plays a significant role, such as neurodegenerative diseases, cardiovascular diseases, and certain types of cancer.
Used in Research and Development:
In the field of research and development, 3-O-Methyl 17α-Estradiol serves as a protected 3-Methoxyestradiol-d5. This protected derivative is valuable for studying the structure-activity relationships of estradiol and its analogs, which can lead to the discovery of new therapeutic agents with improved efficacy and reduced side effects.
Used in Chemical Synthesis:
As a white solid with specific chemical properties, 3-O-Methyl 17α-Estradiol can be used as an intermediate in the synthesis of other steroidal compounds. Its antioxidant activity and structural stability make it a useful building block for creating novel molecules with potential applications in various industries, including pharmaceuticals, cosmetics, and agrochemicals.

Upstream product

• 50-00-0 formaldehyd 
• 1624-62-0 estrone 3-methyl ether 
• 1035-77-4 3-O-methyl-17β-oestradiol 
• 54064-42-5 3-methoxyestra-1,3,5(10)-trien-17β-yl p-toluenesulfonate 
• 127-08-2 potassium acetate 
• 71-23-8 propan-1-ol 
• 17554-55-1 3-methoxy-13α-estra-1,3,5(10)-trien-17-one 
• 6030-83-7 3-Methoxy-oestra-1,3,5⁽¹⁰⁾,7-tetraen-17-on (rac-Equilin-methylaether) 
• 145164-84-7 estradiol 
• 74-88-4 methyl iodide 
• 53-16-7 Estrone 

Downstream Products

• 2394-16-3 3-methoxy-17β-acetoxy-1,3,5(10)-estratriene 
• 1624-62-0 estrone 3-methyl ether 
• 113290-68-9 3-methoxyestra-1,3,5(10)-trien-17α-yl β-benzyloxypropionate 
• 57-91-0 α-estradiol 
• 5738-58-9 (+/-)-3-Methoxy-13β-methyl-8-isogona-2,5(10)-dien-17-one 
• 1091-93-6 (+/-)-3-Methoxy-8α-estra-2,5(10)-dien-17β-ol 
• 14550-57-3 3-methoxy-1,3,5(10)-estratriene 
• 2394-16-3 C₂₁H₂₈O₃ 

Relevant academic research and scientific papers

Direct Synthesis of α-Amino Nitriles from Sulfonamides via Base-Mediated C-H Cyanation

Herein, we disclose a transition-metal-free reaction system that enables α-cyanation of sulfonamides through C-H bond cleavage for the preparation of α-amino nitriles, including difficult-to-access all-alkyl α-tertiary scaffolds. More than 50 substrate examples prove a wide functional group tolerance. Additionally, its synthetic practicality is highlighted by gram-scalability and the late-stage modification of natural compounds. Mechanistic experiments suggest that this process involves in situ formation of an imine intermediate via base-promoted elimination of HF.

Total Synthesis of (-)-C/D-cis-Dehydro-3-O-methyl-estradiols

A convergent synthesis of (-)-dehydro-3-O-methyl-C/D-cis-estradiol started from stereochemically defined substituted optically active 3-(2-arylethyl)-γ-butyrolactones. Regioselective bromination of the anisyl moiety, reductive ring opening of the iodolactone, and protecting-group changes led to a Weinreb amide. This then underwent an intramolecular Grignard reaction closing the B-ring to give a tetralone with defined configuration. Introduction of C-11 through an allyl Grignard addition and subsequent ring-closing metathesis gave a tetrahydro phenanthrene derivative. Oxidation of the side-chain alcohol resulted in the key aldehyde group, and a final samarium-diiodide-mediated reductive D-ring annulation resulted in the generation of the target dehydro-C/D-cis-estradiol derivatives with high stereoselectivity. Structure elucidation was carried out using NOEDS (nuclear Overhauser enhanced differential spectroscopy) analysis on the one hand, and conversion into known 3-O-methyl-13β-estradiols by double-bond hydrogenation on the other. Further efforts to use this estradiol synthetic strategy to generate more complex steroidal natural products and pharmaceutically interesting compounds are in progress.

A simple and convenient synthesis of 2-methoxyestradiol from estrone

A simple and straightforward synthesis of 2-methoxyestradiol have been achieved in nine synthetic steps with 21% of overall yield. Being a convenient process, it can be upscaled to industrial process.

Combined epimerisation and acylation: Meerwein-ponndorf-verley-oppenauer catalysts in action

A practical racemisation-epimerisation method for chiral secondary alcohols has been developed. Meerwein-Ponndorf-Verley-Oppenauer catalysts such as neodymium(III) isopropoxide are able to racemise these alcohols with retention of other stereocentres in the molecule. This is particularly useful for the recycling of the undesired products of kinetic resolutions of alcohols. By combination of such a racemisation with an acylation using isopropenyl or ethoxyvinyl esters as acyl donors, a fast straightforward recycling of starting materials may be achieved. The combined epimerisation and acylation process is demonstrated for the steroid estradiol methyl ether.

Transition metal-catalyzed intramolecular [4+2] cycloadditions: Mechanistic and synthetic investigations

The nickel-catalyzed intramolecular cycloaddition of dienes with unactivatable alkynes is found to proceed under mild conditions while the corresponding Diels-Alder cycloaddition of the same substrates either fails of occurs only under forcing conditions. The nickel-catalyzed cycloaddition is also shown to occur with retention of stereochemistry and is not significantly influenced by electronic effects. Finally, the catalyzed process is shown to be applicable to the synthesis of angularly substituted bicycles, including the CD ring systems of steroids and vitamin D.

Chiral hydrogenation of estrone-3-methyl ether on modified Raney nickel catalysts

The stereochemistry of reduction of the steroid 17-ketone group by Raney nickel catalyst modified by tartaric acid depends on the chirality of the tartaric acid, the pH, and the pressure of hydrogenation. Keywords: chiral reduction; modified Raney nickel catalyst

Homogeneous and heterogeneous catalytic asymmetric reactions II. Asymmetric hydrogenation of steroid ketones

The asymmetric reduction of steroid 17- and 20-ketones with chiral hydrosilanerhodium-(+)-and (-)-diop-complex catalysts allows different stereoselectivities in the formation of 17-alcohols, but not of 20-alcohols.The degree of this stereoselectivity is higher than that attained with other methods.The stereoselectivity can be explained in terms of the most preferred conformation of the α-siloxysteroid-rhodium intermediate complexes.

Steroids, XXXVIII. Neighbouring Group Participation, IX. Preparation of 16α-Hydroxymethyl-3-methoxyestra-1,3,5(10)-trien-17α-ol and Solvolysis Investigations

Solvolysis of the p-toluenesulfonate 1d in acetic acid and in dimethyl sulfoxide yields 5b with inversion at C-17.The conversion can be explained by a neighbouring group participation characterized by the general symbol (AcO-6).In order to confirm the participation of the 16α-acetoxymethyl group in 1d, comparative solvolytic investigations were carried out with the toluenesulfonate 9.

Reduction of Steroid 17-Ketones by Enantiomeric Chiral Reducing Agents

The reduction of steroid 17-ketones by a chiral hydrosilane-rhodium-(-)(2S,3S)-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane reagent allows greater stereoselectivity of 17α-alcohol formation than is obtained by other methods.