57711-44-1

Usage

Uses

Used in Pharmaceutical Industry:
3β-tert-ButyldiMethylsilyloxy Epiandrosterone is used as an intermediate in the synthesis of various steroidal compounds for pharmaceutical applications. Its unique chemical structure allows for the development of new drugs with potential therapeutic benefits in treating hormonal disorders, inflammation, and other conditions related to steroid hormone imbalances.
Used in Research and Development:
In the field of research and development, 3β-tert-ButyldiMethylsilyloxy Epiandrosterone serves as a valuable tool for studying the structure-activity relationships of steroid hormones and their analogs. This knowledge can be applied to design and develop novel steroidal compounds with improved pharmacological properties and reduced side effects.
Used in Analytical Chemistry:
3β-tert-ButyldiMethylsilyloxy Epiandrosterone can be employed as a reference compound in analytical chemistry for the development and validation of methods for the detection and quantification of steroid hormones and their metabolites in biological samples. This is particularly relevant in the fields of sports doping control, endocrinology, and toxicology.
Used in Drug Delivery Systems:
Similar to Gallotannin, 3β-tert-ButyldiMethylsilyloxy Epiandrosterone can be incorporated into drug delivery systems to improve its bioavailability and therapeutic efficacy. By using various organic and metallic nanoparticles as carriers, the compound can be delivered more effectively to target tissues, enhancing its potential applications in the treatment of various medical conditions.

Upstream product

• 481-29-8 Epiandrosterone 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 53-43-0 dehydroepiandrosterone 

Downstream Products

• 53-41-8 (3R,10S,13S)-3-Hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-one 
• 514-33-0 (16S,20S)-3β-hydroxy-23,24-bis-norcholano-22,16-lactone 
• 853904-64-0 16,16,20,20,20-pentadeuterio-3β-{[(1,1-dimethylethyl)dimethylsilanyl]oxy}-17α-methyl-5α-androstan-17β-ol 
• 853904-67-3 16,16,20,20,20-pentadeuterio-3,17β-dihydroxy-17α-methyl-androst-2-ene-2-carboxylic acid methyl ester 
• 853904-65-1 16,16,20,20,20-pentadeuterio-17α-methyl-5α-androstan-3β,17β-diol 

Relevant academic research and scientific papers

Macrocyclic molecular rotors with bridged steroidal frameworks

In this work, we describe the synthesis and solid-state dynamics of isomeric molecular rotors 7E and 7Z, consisting of two androstane steroidal frameworks linked by the D rings by triple bonds at their C17 positions to a 1,4-phenylene rotator. They are also linked by the A rings by an alkenyl diester bridge to restrict the conformational flexibility of the molecules and reduce the number of potential crystalline arrays. The analysis of the resulting molecular structures and packing motifs offered insights of the internal dynamics that were later elucidated by means of line shape analyses of the spectral features obtained through variable-temperature solid-state 13C NMR; such analysis revealed rotations in the solid state occurring at kilohertz frequency at room temperature.

Synthesis of Alkenyl Boronates from Epoxides with Di-[B(pin)]-methane via Pd-Catalyzed Dehydroboration

A practical and broadly applicable catalytic method for the synthesis of (E)-alkenylborons is presented. Reactions are promoted by [Pd(Cl)(η3-C3H5)]2 and proceed by the dehydroboration of cyclic borates. Through

Catalyst-free and metal-free electrophilic bromoamidation of unactivated olefins using the N-bromosuccinimide/sulfonamide Protocol

An efficient, catalyst-free, and metal-free bromoamidation of unactivated olefins has been developed. 4-(Trifluoromethyl)benzenesulfonamide and N-bromosuccinimide were used as the nitrogen and halogen sources, respectively. The methodology is applicable to both cyclic and aliphatic olefins.

Novel steroid inhibitors of glucose 6-phosphate dehydrogenase

Novel derivatives of the steroid DHEA 1, a known uncompetitive inhibitor of G6PD, were designed, synthesized, and tested for their ability to inhibit this dehydrogenase enzyme. Several compounds with approximately 10-fold improved potency in an enzyme assay were identified, and this improved activity translated to efficacy in a cellular assay. The SAR for steroid inhibition of G6PD has been substantially developed; the 3β-alcohol can be replaced with 3β-H-bond donors such as sulfamide, sulfonamide, urea, and carbamate. Improved potency was achieved by replacing the androstane nucleus with a pregnane nucleus, provided a ketone at C-20 is present. For pregnan-20-ones incorporation of a 21-hydroxyl group is often beneficial. The novel compounds generally have good physicochemical properties and satisfactory in vitro DMPK parameters. These derivatives may be useful for examining the role of G6PD inhibition in cells and will assist the future design of more potent steroid inhibitors with potential therapeutic utility.

First synthesis of a pentadeuterated 3′-hydroxystanozolol - An internal standard in doping analysis

The first synthesis of 16,16,20,20,20-pentadeuterio-3′- hydroxystanozolol (8) in 26% yield over nine steps is described using moderately priced starting materials and economic amounts of reagents. Compound 8 can be used as an internal standard in screening procedures for anabolic steroids as well as for the quantification of stanozolol metabolites via mass spectrometric techniques, such as LC-MS or gas chromatography-mass spectrometry (GC-MS).

Stereospecific synthesis of steroidal 20,16-γ-carbolactones

Two strategies have been explored for the synthesis of steroidal 20,16- γ-carbolactones from the corresponding 17-ketoandrostane. A highly efficient, stereospecific protocol has been developed for the β-oriented cis-γ-lactone, based on a Michael addition of cyanide to a conjugated ketone. A different approach, involving prior attachment of a 3-carbon side chain on C-17 of a 17-oxo-16β-acetoxy-androstane led to the epimeric, α- oriented lactone.