methyl 17β-(tert-butyldimethylsilyloxy)-2-phenylseleno-5,5-ethylenedioxy-3,5-seco-4-norandrostan-3-oate

Base Information

• Chemical Name: methyl 17β-(tert-butyldimethylsilyloxy)-2-phenylseleno-5,5-ethylenedioxy-3,5-seco-4-norandrostan-3-oate
• CAS No.: 326864-87-3
• Molecular Formula: C₃₃H₅₂O₅SeSi
• Molecular Weight: 635.818
• Mol file: 326864-87-3.mol

Synonyms:

Chemical Property of methyl 17β-(tert-butyldimethylsilyloxy)-2-phenylseleno-5,5-ethylenedioxy-3,5-seco-4-norandrostan-3-oate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 17β-(tert-butyldimethylsilyloxy)-2-phenylseleno-5,5-ethylenedioxy-3,5-seco-4-norandrostan-3-oate

There total 6 articles about methyl 17β-(tert-butyldimethylsilyloxy)-2-phenylseleno-5,5-ethylenedioxy-3,5-seco-4-norandrostan-3-oate 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:

diphenyl diselenide (1666-13-3) + methyl 17β-(tert-butyldimethylsilyloxy)-5,5-ethylenedioxy-3,5-seco-4-norandrostan-3-oate (326864-57-7) → methyl 17β-(tert-butyldimethylsilyloxy)-2-phenylseleno-5,5-ethylenedioxy-3,5-seco-4-norandrostan-3-oate (326864-87-3)

Guidance literature:

methyl 17β-(tert-butyldimethylsilyloxy)-5,5-ethylenedioxy-3,5-seco-4-norandrostan-3-oate; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.416667h;

diphenyl diselenide; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1016/S0040-4020(00)00966-2

Reference yield:

testosterone propionate (57-85-2) → methyl 17β-(tert-butyldimethylsilyloxy)-2-phenylseleno-5,5-ethylenedioxy-3,5-seco-4-norandrostan-3-oate (326864-87-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: O₃ / ethyl acetate / -78 °C

1.2: 87 percent / H₂O₂ / H₂O / 20 °C

2.1: 88 percent / KOH / methanol; H₂O / 3 h / Heating

3.1: methanol

4.1: 74 percent / trimethyl orthoformate; PTSA / 20 °C

5.1: 99 percent / imidazole / dimethylformamide / 20 °C

6.1: LDA / tetrahydrofuran / 0.42 h / -78 °C

6.2: 1.869 g / tetrahydrofuran / -78 - 20 °C

With 1H-imidazole; potassium hydroxide; toluene-4-sulfonic acid; ozone; lithium diisopropyl amide; trimethyl orthoformate; In tetrahydrofuran; methanol; water; ethyl acetate; N,N-dimethyl-formamide; 1.1: ozonolysis / 1.2: Reduction / 2.1: Hydrolysis / 3.1: Methylation / 4.1: Cyclization / 5.1: silylation / 6.1: Metallation / 6.2: Substitution;

DOI:10.1016/S0040-4020(00)00966-2

Reference yield:

5-oxo-A-nor-3,5-seco-17β-hydroxy-androstan-3-oic acid (1759-35-9) → methyl 17β-(tert-butyldimethylsilyloxy)-2-phenylseleno-5,5-ethylenedioxy-3,5-seco-4-norandrostan-3-oate (326864-87-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: methanol

2.1: 74 percent / trimethyl orthoformate; PTSA / 20 °C

3.1: 99 percent / imidazole / dimethylformamide / 20 °C

4.1: LDA / tetrahydrofuran / 0.42 h / -78 °C

4.2: 1.869 g / tetrahydrofuran / -78 - 20 °C

With 1H-imidazole; toluene-4-sulfonic acid; lithium diisopropyl amide; trimethyl orthoformate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 1.1: Methylation / 2.1: Cyclization / 3.1: silylation / 4.1: Metallation / 4.2: Substitution;

DOI:10.1016/S0040-4020(00)00966-2

upstream raw materials:

diphenyl diselenide

methyl 17β-(tert-butyldimethylsilyloxy)-5,5-ethylenedioxy-3,5-seco-4-norandrostan-3-oate

testosterone propionate

5-oxo-A-nor-3,5-seco-17β-hydroxy-androstan-3-oic acid