4999-76-2

Basic information

• Product Name: 3,17β-Diacetoxy-3,5-estradiene
• Synonyms: (17β)-Estra-3,5-diene-3,17-diol 3,17-Diacetate;(17β)-Estra-3,5-diene-3,17-diol Diacetate;3,17β-Diacetoxy-3,5-estradiene;GAIRDOKUNQTVPZ-ZCPXKWAGSA-N
• CAS NO: 4999-76-2
• Molecular Formula: C₂₂H₃₀O₄
• Molecular Weight: 358.4712
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
• Mol File: 4999-76-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,17β-Diacetoxy-3,5-estradiene(CAS DataBase Reference)
• NIST Chemistry Reference: 3,17β-Diacetoxy-3,5-estradiene(4999-76-2)
• EPA Substance Registry System: 3,17β-Diacetoxy-3,5-estradiene(4999-76-2)

Safety Data

• Hazardous Substances Data: 4999-76-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3,17β-Diacetoxy-3,5-estradiene is used as an intermediate compound for the synthesis of various steroidal drugs. Its chemical structure allows for the modification and creation of a wide range of steroidal medications, including hormones, anti-inflammatory drugs, and contraceptives.
Used in Chemical Industry:
In the chemical industry, 3,17β-Diacetoxy-3,5-estradiene serves as a key building block for the production of other steroidal compounds. Its versatility in chemical reactions enables the synthesis of various complex steroidal molecules with specific applications in different fields.
Used in Research and Development:
3,17β-Diacetoxy-3,5-estradiene is also utilized in research and development for the study of steroidal compounds and their biological effects. Its unique structure provides valuable insights into the design and development of new drugs and pharmaceuticals with improved efficacy and safety profiles.

Upstream product

• 108-22-5 Isopropenyl acetate 
• 108-21-4 Isopropyl acetate 
• 434-22-0 19-nortestosterone 
• 1091-93-6 3-methoxy-17-hydroxyestra-2,5⁽¹⁰⁾-diene 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 

Downstream Products

• 415927-29-6 3-oxo-7α-[9-(4,4,5,5,5-pentafluoropentylsulfanyl)nonyl]estra-4-en-17βyl acetate 
• 1239977-74-2 3-oxo-7β-[9-(4,4,5,5,5-pentafluoropentylsulfanyl)nonyl]estra-4-en-17βyl acetate 
• 875573-69-6 17-O-acetyl-S-deoxo-fulvestrant 
• 129453-61-8 fulvestrant 
• 153004-31-0 (+)-(7α)-[9-(4,4,5,5,5-pentafluoropentylsulfanyl)nonyl]estra-1,3,5(10)-triene-3,17β-diol 
• 3764-87-2 7α-methyl-19-nortestosterone 
• 54793-00-9 17β-hydroxy-7α-methyl-estr-5-en-3-one acetate 
• 6157-87-5 7alpha-Methyl-19-nortestosterone acetate 
• 115759-24-5 (3S)-3,17β-bis-(3,5-dinitro-benzoyloxy)-9,10-seco-estra-5(10),6t,8-triene 
• 3434-45-5 6-oxo-3,17β-estradiol diacetate 
• 6599-92-4 17β-acetoxy-3-hydroxy-1,3,5(10)-estratriene-6-one 
• 25975-59-1 3β,17β-dihydroxy-19-norandrost-5-ene 
• 1425-10-1 19-nortestosterone acetate 
• 18119-95-4 17β-acetoxy-6β-fluoro-4-estren-3-one 

Relevant articles and documents

METHODS OF TREATING ADVANCED PROSTATE CANCER

Provided herein are methods for treating metastatic prostate cancer using anti-androgen compounds and radionuclide-labeled androgens.

Preparation method for 3,5-estradiene-3,17beta-diacetate

The invention relates to a preparation method for 3,5-estradiene-3,17beta-diacetate. The preparation method comprises the following steps: sequentially adding nandrolone, p-toluenesulfonic acid monohydrate, isopropyl acetate and magneton No. 15 into a reactor, introducing condensed water, carrying out a heating reaction in an oil-bath pot and slowing adding isopropenyl acetate when reflux condensation of the obtained system begins; after completion of a reaction, carrying out evaporation to remove a solvent; cooling the system, adding pyridine, and adding isopropanol drop by drop until a white solid product is precipitated; carrying out low-temperature cooling and pumping filtration and then carrying out cleaning with cold isopropanol; collecting the white solid product and then carrying out drying so as to obtain a pure 3,5-estradiene-3,17beta-diacetate product. According to the invention, nandrolone is used as a substrate and a one-pot method is employed for carbonyl and hydroxyl acetylation protection so as to synthesize the product; the method is simple in process, mild in conditions and friendly to environment and has yield of up to 85%; and the synthesized product has critical application value in the fields of medicines, veterinary drugs and pesticides and is an important pro-drug for tibolone.

PROCESS AND INTERMEDIADES FOR THE PREPARATION OF 7-ALKYLATED STEROIDS

A process for preparing compounds of formula (I), or a salt, solvate or stereoisomer thereof, including Fulvestrant, which process comprises free radical to a compound of formula (III), or a salt, solvate or stereoisomer thereof. The invention also refers to intermediates of said process.

Stereoselective synthesis of some methyl-substituted steroid hormones and their in vitro cytotoxic activity against human gastric cancer cell line MGC-803

A series of 3-, 7-, 15-, and 16-methyl-substituted steroid analogs were synthesized via a highly stereoselective 1,6-conjugate addition. Under the catalysis of CuBr, AlMe3 reacted with four steroid dienone precursors to afford either the corresponding α-epimer of C-3 and C-7 methyl-substituted steroids as the major products, and the ratio of α/β was up to 10/1. No β-epimer has been detected for methyl addition at C-16. However, under the same reaction conditions, enantioselective methyl addition at C-15 afforded the 15β-epimer as the major product. The preliminary SAR analysis showed that the methyl substituents at C-7α and C-15β positions lead to a dramatical increase in potency against human gastric cancer cell line MGC-803.

Molecular iodine in isopropenyl acetate (IPA): a highly efficient catalyst for the acetylation of alcohols, amines and phenols under solvent free conditions

Iodine in isopropenyl acetate (IPA) is a highly efficient catalyst for the acetylation of a variety of alcohols, phenols and amines under solvent free conditions. Primary, secondary, tertiary alcohols, amines and mono to polyhydroxy phenols and anilines with electron donating or withdrawing substituents can be easily acetylated in good to excellent yield at 85-90 °C.

PROCESS FOR THE PRODUCTION OF TIBOLONE

Disclosed is a process for the synthesis of 17β-hydroxy-7α-methyl- 19-nor-17α-pregn-5(10)-ene-20-yne-3-one (tibolone, 11) and intermediates useful for the synthesis thereof: (11).

Optimization of copper(I)-catalyzed 1,6-conjugate addition of a methyl group to 17β-acetoxy-4,6-estradien-3-one

7α-Methyl-19-nortestosterone (1) was synthesized from 19-nortestosterone (2) via 17β-acetoxy-4,6-estradien-3-one (4). The critical parameters for the synthesis of compound (1) have been identified. An optimization procedure consisting of an iterative, two-stage reaction response surface analysis was carried out. As a result, the synthesis of the target compound (1) from the intermediate (4) was achieved under the newly determined conditions, in a repeatable manner. This afforded compound (1) in an yield of over 60%, essentially free from the 7β-Me isomer (6), under experimental conditions amenable for scale enhancement.

Improved syntheses of 3,17β-diacetoxyestra-1,3,5(10)-trien-6-one

Improved syntheses of 3,17β-Diacetoxyestra-1,3,5(10)-trien-6-one 5 was achieved in 4 steps (respectively in 45% and 56% overall yield) from 19-nortestosterone 1.

Synthesis of C-6 fluoroandrogens: Evaluation of ligands for tumor receptor imaging

Seven androgens, substituted with fluorine at C-6, were prepared as potential imaging agents for androgen receptor-positive prostate tumors and were evaluated in vitro in terms of their lipophilicity and their relative binding affinities (RBA, relative to R1881 = 100) for the androgen receptor and for sex steroid binding protein.Introduction of a fluorine atom into the C-6 position of an androgen generally decreases binding affinity to the androgen receptor, except in the two cases: 6α-fluoro-19-nor-testosterone RBA = 41.6 versus 30.6 for the unsubstituted steroid) and 6α-fluorotestosterone (RBA = 8.9 versus 6.6).Receptor binding of the C-6 fluoro-androgens is also stereospecific, showing higher binding affinities for the α-epimers compared to the corresponding β-epimers (4:1 - 15:1).Binding affinity to sex steroid binding protein is the lowest with 19-nor-testosterone, which is also the least lipophilic androgen studied.Based on the binding properties of compounds in this series, 6α-fluoro-19-nor-testosterone appears to have the most promise as a tumor imaging agent. - Keywords: C-6-fluoroandrogens; fluorine substitution; relative binding affinity; 6α- and 6β-epimers; log Po/w; prostate tumors

The Preparation of 7α- and 7β-Allyloestradiol, and an Unusual Titanium(IV) Chloride Mediated Dimerisation

17β-Acetoxyoestra-4,6-dien-3-one reacts with allyltrimethylsilane in the presence of fluoride ion to give the 7α- and 7β-allyloestr-4-en-3-ones in low yield.With titanium(IV) chloride catalysis, the 7α-allyloestr-4-en-3-one is the only product at -78 deg C, but its novel 6β,6'β-'dimer' is also formed at higher temperatures.The isomeric 7-allyloestr-4-en-3-ones have been aromatised to give 7α- and 7β-allyloestradiols.