4-{(S)-1-[(1S,3R,9S,10R,13S,14R)-1,3-Bis-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-ethoxy}-2-methyl-butan-2-ol

Base Information

• Chemical Name: 4-{(S)-1-[(1S,3R,9S,10R,13S,14R)-1,3-Bis-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-ethoxy}-2-methyl-butan-2-ol
• CAS No.: 103909-78-0
• Molecular Formula: C₃₈H₇₀O₄Si₂
• Molecular Weight: 647.142
• Mol file: 103909-78-0.mol

Synonyms:4-{(S)-1-[(1S,3R,9S,10R,13S,14R)-1,3-Bis-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-ethoxy}-2-methyl-butan-2-ol

Chemical Property of 4-{(S)-1-[(1S,3R,9S,10R,13S,14R)-1,3-Bis-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-ethoxy}-2-methyl-butan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-{(S)-1-[(1S,3R,9S,10R,13S,14R)-1,3-Bis-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-ethoxy}-2-methyl-butan-2-ol

There total 2 articles about 4-{(S)-1-[(1S,3R,9S,10R,13S,14R)-1,3-Bis-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-ethoxy}-2-methyl-butan-2-ol 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(tert-butyldimethylsilyloxy)-20(S)-(3-hydroxy-3-methylbutyloxy)pregna-5,7-diene (103909-78-0)

Guidance literature:

Multi-step reaction with 8 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 / tetrahydrofuran; mineral oil / 20 °C / Large scale

5.2: 1 h / 20 °C / Reflux; Large scale

6.1: L-Selectride / tetrahydrofuran / 1 h / Reflux; Large scale

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

8.1: 2,4,6-trimethyl-pyridine / toluene / 2.5 h / 110 °C / Large scale

With 1H-imidazole; 2,4,6-trimethyl-pyridine; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; dihydrogen peroxide; L-Selectride; sodium hydride; sodium hydroxide; In tetrahydrofuran; n-heptane; N,N-dimethyl-formamide; toluene; mineral oil; 2.1: |Wittig Olefination;

DOI:10.1021/op049822x

Reference yield:

1α,3β-dihydroxy-androst-5-en-17-one (20998-18-9) → 4-{(S)-1-[(1S,3R,9S,10R,13S,14R)-1,3-Bis-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-ethoxy}-2-methyl-butan-2-ol (103909-78-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 94 percent / imidazole, 1-hydroxybenzotriazole / dimethylformamide / 72 h / 50 - 60 °C

2: 1.) NBS; 2.) γ-collidine / 1.) hexane, reflux, 1 h; 2.) xylene, reflux, 1 h

3: 64 percent / dimethylsulfoxide; tetrahydrofuran / Ambient temperature

4: 1.) 9-BBN; 2.) NaOH, H₂O₂ / 1.) THF, r.t., 16 h

5: 1.) NaH; 2.) O₂, PdCl₂, CuCl / 1.) xylene, reflux, 18 h; 2.) DMF-H₂O, r.t. 19 h

6: 79 percent / tetrahydrofuran / 1 h / 0 °C

With 1H-imidazole; 2,4,6-trimethyl-pyridine; sodium hydroxide; N-Bromosuccinimide; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide; oxygen; sodium hydride; benzotriazol-1-ol; copper(l) chloride; palladium dichloride; In tetrahydrofuran; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1248/cpb.34.4410

Reference yield: 85.0%

1α,3β-bis(tert-butyldimethylsilyloxy)-20(S)-(3-hydroxy-3-methylbutyloxy)pregna-5,7-diene (103909-78-0) → 1α,3β-dihydroxy-20(S)-(3-hydroxy-3-methylbutyloxy)pregna-5,7-diene (142785-61-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 18h; Heating;

DOI:10.1248/cpb.40.1494

upstream raw materials:

1α,3β-dihydroxy-androst-5-en-17-one

Downstream raw materials:

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

1α,25-dihydroxy-22-oxavitamin D₃

maxacalcitol

(5Z,7E)-(1S,3R)-1,25-dihydroxy-22-oxa-9,10-secocholesta-5,7,10⁽¹⁹⁾-trien-3-yl hemiglutarate

Refernces

• 1、 Murayama,Miyamoto,Kubodera,Mori,Matsunaga. "Synthetic studies of vitamin D3 analogues. VIII. Synthesis of 22-oxavitamin D3 analogues". . p. 4410 - 4413. Retrieved 2007/10/02.