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Usage

Uses

Used in Pharmaceutical Industry:
3-O-Methyl-6-oxo 17β-Estradiol is used as a key intermediate in the synthesis of contraceptive steroids. As an estradiol derivative, it plays a crucial role in the development and production of hormonal contraceptives, which are essential for family planning and reproductive health.
Used in Contraceptive Steroid Preparation:
In the pharmaceutical industry, 3-O-Methyl-6-oxo 17β-Estradiol is utilized as a starting material for the preparation of contraceptive steroids. Its chemical structure allows for the creation of various steroidal compounds that can be used in the formulation of birth control pills, patches, and other contraceptive methods. These contraceptives help in regulating hormone levels and preventing ovulation, thus providing a reliable means of contraception.

Upstream product

• 571-92-6 6-ketoestradiol 
• 77-78-1 dimethyl sulfate 
• 434-22-0 19-nortestosterone 
• 74-88-4 methyl iodide 
• 434-22-0 19-nortestosterone 
• 67-56-1 methanol 
• 473882-84-7 3-methoxy-17β-(2-tetrahydropyranyloxy)estra-1,3,5-trien-6-ol 
• 147802-61-7 6-oxoestra-1,3,5(10)-triene-3,17β-diyl dipropionate 
• 174497-42-8 (8R,9S,13S,14S,17S)-3-Methoxy-13-methyl-17-(tetrahydro-pyran-2-yloxy)-7,8,9,11,12,13,14,15,16,17-decahydro-cyclopenta[a]phenanthren-6-one 
• 1963-36-6 4-methoxycinnamaldehyde 
• 1020110-71-7 2-methyl-2-(2-nitroethyl)-1,3-cyclopentanedione 

Downstream Products

• 107612-16-8 6-Phenyl-estra-1,3,5(10),6-tetraene-3,17β-diol 3-methyl ether 
• 1035-77-4 3-O-methyl-17β-oestradiol 
• 7291-47-6 3-Methoxy-6α,17β-dihydroxy-oestratrien-<1,3,5(10)> 
• 107612-19-1 6α-(p-benzyloxyphenyl)-6β-hydroxy-estra-1,3,5(10)-triene-3,17β-diol 3-methyl ether 
• 107612-18-0 6β-(p-Benzyloxyphenyl)-6α-hydroxy-estra-1,3,5(10)-triene-3,17β-diol 3-methyl ether 

Relevant academic research and scientific papers

Synthesis of (3alpha,7beta,17alpha)-7-methyl-19-norpregn-5(10)-en-20-yne-3,7,17-triol, a metabolite of ORG OD14, and its 7-epimer.

The syntheses of the 7beta-hydroxy metabolite of ORG OD14 (Livial((R))), (3alpha,7beta,17alpha)-7-methyl-19-norpregn-5(10)-en-20-yne-3,7,17-triol (35), and its 7-epimer, (3alpha,7alpha,17alpha)-7-methyl-19-norpregn-5(10)-en-20-yne-3,7,17-triol (11), are described.

Synthesis and Unusual Beckmann Fragmentation Reaction of syn-3-Methoxy-6α,17β-Dihydroxyestra-1,3,5(10)-trien-7-one Oxime

Sodium borohydride reduction of anti-3-methoxy-17β-hydroxyestra-1,3,5(10)-trien-6,7-dione 7-oxime (4a) afforded syn-3-methoxy-6α,17β-dihydroxyestra-1,3,5(10)-trien-7-one oxime (5), which in thionyl chloride at -18 deg C underwent Beckmann fragmentation re

Synthesis of (3α,7β,17α)-7-methyl-19-norpregn-5(10)-en-20-yne-3,7,17- triol, a metabolite of ORG OD14, and its 7-epimer

The syntheses of the 7β-hydroxy metabolite of ORG OD14 (Livial), (3α,7β,17α)-7-methyl-19-norpregn-5(10)-en-20-yne-3,7,17-triol (35), and its 7-epimer, (3α,7α,17α)-7-methyl-19-norpregn-5(10)-en-20-yne-3,7,17- triol (11), are described. (C) 2000 Elsevier Science Inc.

Total Synthesis of Estradiol Methyl Ether and Its Five-Pot Synthesis with an Organocatalyst

Enantioselective total synthesis of estradiol methyl ether has been accomplished in a highly diastereo- and enantioselective manner. The key reaction is diphenylprolinol silyl ether mediated domino Michael/aldol reaction to afford bicyclo[4.3.0]nonane derivatives with A, C, and D rings of the steroids as a single isomer with excellent enantioselectivity. Each reaction was optimized, and the total synthesis could be accomplished in 12 pots with 10 purifications using silica gel, resulting in an overall yield of 6.8 %. The reaction sequence and reaction conditions were then optimized in terms of pot economy, whereupon estradiol methyl ether could be synthesized using five reaction vessels with four purifications in an overall yield of 15 %. Notably, six reactions, namely, oxidation, hydrogenation, formation of acid chloride, Friedel–Crafts reaction, deprotection, and reduction could be carried out in the last one-pot sequence.

PROCESS FOR THE PREPARATION OF STEROID DERIVATIVES

A method of producing 3-alkoxy-1,3,5(10)-triene-6-one-steroid derivatives having, in the steroid skeleton thereof, a partial structure of A- and B-rings represented by formula (2) : (wherein R represents an alkyl group, a cycloalkyl group, an alkenyl group, or an aralkyl group), including reacting a 19-norsteroid derivative having, in the steroid skeleton thereof, a partial structure of A- and B-rings represented by formula (1) : with an alcohol represented by ROH (wherein R has the same meaning as defined above) and iodine in the absence of a rare earth compound catalyst. According to the method of the present invention, 3-alkoxy-1,3,5(10)-triene-6-one-steroids can be selectively produced from 19-norsteroides through a single reaction step without employment of a special catalyst.

6-Oxoestradiols from estradiols: Exploiting site selective metalation of aralkyl systems with superbases

3-O-Protected estradiol derivatives undergo metalation at C-6 when exposed to a fourfold excess of the reagent consisting of an equimolar mixture of lithium diisopropylamide and potassium 1,1-dimethylpropoxide (3 h, THF, -78°C). The metalated intermediates can be oxidized by quenching with trimethyl borate followed by treatment with hydrogen peroxide, thus allowing the introduction of a 6-hydroxy group into the estradiol framework. Further oxidation of the 6-hydroxy group gives O-protected 6-oxoestradiols.