1α,3β-bis(t-butyldimethylsilyloxy)-20S-(3-oxobutyloxy)-5-pregnene

Base Information

• Chemical Name: 1α,3β-bis(t-butyldimethylsilyloxy)-20S-(3-oxobutyloxy)-5-pregnene
• CAS No.: 854481-65-5
• Molecular Formula: C₃₇H₆₈O₄Si₂
• Molecular Weight: 633.116
• Mol file: 854481-65-5.mol

Synonyms:1α,3β-bis(t-butyldimethylsilyloxy)-20S-(3-oxobutyloxy)-5-pregnene

Chemical Property of 1α,3β-bis(t-butyldimethylsilyloxy)-20S-(3-oxobutyloxy)-5-pregnene

Chemical Property:

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1α,3β-bis(t-butyldimethylsilyloxy)-20S-(3-oxobutyloxy)-5-pregnene

There total 1 articles about 1α,3β-bis(t-butyldimethylsilyloxy)-20S-(3-oxobutyloxy)-5-pregnene 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:

1α,3β-dihydroxy-androst-5-en-17-one (20998-18-9) → 1α,3β-bis(t-butyldimethylsilyloxy)-20S-(3-oxobutyloxy)-5-pregnene (854481-65-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 6 h / 20 - 125 °C / Large scale

2.1: potassium tert-butylate / tetrahydrofuran / 4 h / 25 - 30 °C / Large scale

3.1: tetrahydrofuran / 4 h / 20 - 45 °C / Large scale

4.1: sodium hydroxide; dihydrogen peroxide / 1 h / 25 °C / Large scale

5.1: sodium hydride; 15-crown-5 / tetrahydrofuran; mineral oil / 6 h / 0 °C / Large scale

6.1: cerium(III) chloride / tetrahydrofuran / 0.5 h / -15 °C

6.2: 0.5 h / -15 °C

With 1H-imidazole; cerium(III) chloride; 15-crown-5; potassium tert-butylate; dihydrogen peroxide; sodium hydride; sodium hydroxide; In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil; 2.1: |Wittig Olefination;

DOI:10.1021/op049822x

Reference yield:

1α,3β-bis(t-butyldimethylsilyloxy)-20S-(3-oxobutyloxy)-5-pregnene (854481-65-5) → maxacalcitol (103909-75-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: cerium(III) chloride / tetrahydrofuran / 0.5 h / -15 °C / Large scale

1.2: 0.5 h / -15 °C / Large scale

2.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / n-heptane / 0.25 h / 78 °C

3.1: 2,4,6-trimethyl-pyridine / toluene / 2.5 h / 110 °C / Large scale

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 9 h / 66 °C

5.1: tetrahydrofuran / 7 h / 10 °C / Irradiation

6.1: tetrahydrofuran / 85 h / 25 °C

With 2,4,6-trimethyl-pyridine; N-Bromosuccinimide; cerium(III) chloride; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; In tetrahydrofuran; n-heptane; toluene;

DOI:10.1021/op049822x

Reference yield:

1α,3β-bis(t-butyldimethylsilyloxy)-20S-(3-oxobutyloxy)-5-pregnene (854481-65-5) → C26H42O4

Guidance literature:

Multi-step reaction with 5 steps

1.1: cerium(III) chloride / tetrahydrofuran / 0.5 h / -15 °C / Large scale

1.2: 0.5 h / -15 °C / Large scale

2.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / n-heptane / 0.25 h / 78 °C

3.1: 2,4,6-trimethyl-pyridine / toluene / 2.5 h / 110 °C / Large scale

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 9 h / 66 °C

5.1: tetrahydrofuran / 7 h / 10 °C / Irradiation

With 2,4,6-trimethyl-pyridine; N-Bromosuccinimide; cerium(III) chloride; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; In tetrahydrofuran; n-heptane; toluene;

DOI:10.1021/op049822x

upstream raw materials:

1α,3β-dihydroxy-androst-5-en-17-one

Downstream raw materials:

maxacalcitol

1α,3β-dihydroxy-20(S)-(3-hydroxy-3-methylbutyloxy)pregna-5,7-diene

Refernces