Epiandrosterone, TBDMSi (3-O)

Base Information

• Chemical Name: Epiandrosterone, TBDMSi (3-O)
• CAS No.: 57711-44-1
• Molecular Formula: C25H44O2Si
• Molecular Weight: 404.70116
• DSSTox Substance ID: DTXSID30448618
• Nikkaji Number: J530.728G
• Wikidata: Q82267695
• Mol file: 57711-44-1.mol

Synonyms:Epiandrosterone, TBDMSi (3-O);57711-44-1;(3S,5S,8R,9S,10S,13S,14S)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one;Androstan-17-one, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (3.beta.,5.alpha.)-;5.alpha.-Androstan-3.beta.-ol-17-one, TBDMS derivative;3-([tert-Butyl(dimethyl)silyl]oxy)androstan-17-one-, (3.beta.,5.alpha.)-;DTXSID30448618;UGWVQACEZWDYMD-YMKPZFJOSA-N;3beta-[[Dimethyl(tert-butyl)silyl]oxy]-5alpha-androstan-17-one

Chemical Property of Epiandrosterone, TBDMSi (3-O)

Chemical Property:

• PSA: 26.30000
• LogP: 6.98860
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 404.31105718
• Heavy Atom Count: 28
• Complexity: 635

Purity/Quality:

98% ^*data from raw suppliers

3b-tert-Butyldimethylsilyloxy epiandrosterone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(CC1CCC3C2CCC4(C3CCC4=O)C)O[Si](C)(C)C(C)(C)C
• Isomeric SMILES: C[C@]12CC[C@@H](C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C)O[Si](C)(C)C(C)(C)C
• Uses: Protected Epi Androsterone (E578000). A steroid hormone that is present in normal human urine. Less active 3β-isomer of the androgen Androsterone (A635535). Controlled Substance.

Technology Process of Epiandrosterone, TBDMSi (3-O)

There total 3 articles about Epiandrosterone, TBDMSi (3-O) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

Epiandrosterone (481-29-8) + tert-butyldimethylsilyl chloride (18162-48-6) → (3S,10S,13S)-3-((tert-butyldimethylsilyl)oxy)-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta-[a]phenanthren-17-one (57711-44-1)

Guidance literature:

With 1H-imidazole; In dichloromethane; for 0.5h;

DOI:10.1016/j.steroids.2004.10.002

Reference yield: 90.0%

Epiandrosterone (481-29-8) + t-butyldimethylsiyl triflate (69739-34-0) → (3S,10S,13S)-3-((tert-butyldimethylsilyl)oxy)-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta-[a]phenanthren-17-one (57711-44-1)

Guidance literature:

With pyridine; In dichloromethane; Cooling with ice;

DOI:10.1021/jm300317k

Reference yield:

dehydroepiandrosterone (53-43-0) → (3S,10S,13S)-3-((tert-butyldimethylsilyl)oxy)-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta-[a]phenanthren-17-one (57711-44-1)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium on activated charcoal; hydrogen / ethanol

2: pyridine / dichloromethane / Cooling with ice

With pyridine; palladium on activated charcoal; hydrogen; In ethanol; dichloromethane;

DOI:10.1021/jm300317k

upstream raw materials:

Epiandrosterone

tert-butyldimethylsilyl chloride

t-butyldimethylsiyl triflate

dehydroepiandrosterone

Downstream raw materials:

(3R,10S,13S)-3-Hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-one

(16S,20S)-3β-hydroxy-23,24-bis-norcholano-22,16-lactone

16,16,20,20,20-pentadeuterio-3β-{[(1,1-dimethylethyl)dimethylsilanyl]oxy}-17α-methyl-5α-androstan-17β-ol

16,16,20,20,20-pentadeuterio-3,17β-dihydroxy-17α-methyl-androst-2-ene-2-carboxylic acid methyl ester

Refernces

• 1、 Murray, Stephanie A.,Luc, Eugenia C. M.,Meek, Simon J.. "Synthesis of Alkenyl Boronates from Epoxides with Di-[B(pin)]-methane via Pd-Catalyzed Dehydroboration". supporting information. p. 469 - 472. Retrieved 2018/01/28.
• 2、 Hamilton, Niall M.,Dawson, Martin,Fairweather, Emma E.,Hamilton, Nicola S.,Hitchin, James R.,James, Dominic I.,Jones, Stuart D.,Jordan, Allan M.,Lyons, Amanda J.,Small, Helen F.,Thomson, Graeme J.,Waddell, Ian D.,Ogilvie, Donald J.. "Novel steroid inhibitors of glucose 6-phosphate dehydrogenase". supporting information; experimental part. p. 4431 - 4445. Retrieved 2012/09/11.