(20R,22R)-3β-t-butyldimethylsilyloxy-5α,20-dihydroxy-6β-phenylthio-1-oxowith-24-enolide

Base Information

• Chemical Name: (20R,22R)-3β-t-butyldimethylsilyloxy-5α,20-dihydroxy-6β-phenylthio-1-oxowith-24-enolide
• CAS No.: 90525-27-2
• Molecular Formula: C₄₀H₆₀O₆SSi
• Molecular Weight: 697.064
• Mol file: 90525-27-2.mol

Synonyms:(20R,22R)-3β-t-butyldimethylsilyloxy-5α,20-dihydroxy-6β-phenylthio-1-oxowith-24-enolide

Chemical Property of (20R,22R)-3β-t-butyldimethylsilyloxy-5α,20-dihydroxy-6β-phenylthio-1-oxowith-24-enolide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (20R,22R)-3β-t-butyldimethylsilyloxy-5α,20-dihydroxy-6β-phenylthio-1-oxowith-24-enolide

There total 18 articles about (20R,22R)-3β-t-butyldimethylsilyloxy-5α,20-dihydroxy-6β-phenylthio-1-oxowith-24-enolide 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:

Pregnenolone (145-13-1) → (20R,22R)-3β-t-butyldimethylsilyloxy-5α,20-dihydroxy-6β-phenylthio-1-oxowith-24-enolide (90525-27-2)

Guidance literature:

Multi-step reaction with 17 steps

1: 28 g / NaBH₄ / methanol; tetrahydrofuran / 0.67 h / 0 °C

2: 61 percent / dichlorodicyanobenzoquinone / dioxane / 8 h / Heating

3: toluene-p-sulphonic acid / CH₂Cl₂ / 3 h / Ambient temperature

4: 83 percent / 30percent H₂O₂, NaOH / methanol / 15 °C

5: 1.) liquid NH₃, Li, 2.) NH₄Cl / 1.) THF, -78 deg C -> -40 deg C, 20 min, 2.) 2 h

6: N,N-diethylcyclohexylamine / dioxane / 6 h / Heating

7: 2M HCl / methanol / 2 h / Ambient temperature

8: 80 percent / pyridinium chlorochromate, AcONa / CH₂Cl₂ / 3 h / Ambient temperature

9: 1.) n-BuLi / 1.) THF, - 5 deg C, 2.) -5 deg C, 8 h

10: 85 percent / HgO, BF₃-ether / tetrahydrofuran / 0.5 h / Heating

11: 81 percent / N,N-diethylcyclohexylamine / dioxane / 8 h / Heating

12: 1.) LDA, HMPA / 1.) THF, - 78 deg C, 1 h, 2.) -78 deg C, 6 h

13: 82 percent / 6M HCl / tetrahydrofuran / 3 h / Ambient temperature

14: 90 percent / imidazole / dimethylformamide / 1 h / Ambient temperature

15: 76 percent / m-chloroperbenzoic acid / CHCl₃ / 0.67 h / -5 °C

16: 80 percent / pyridinium dichromate / dimethylformamide / 8 h / -5 °C

17: 1.) alumina Woelm N-20 / 1.) Et₂O, room tempereature, 20 min, 2.) Et₂O-THF, room temperature, 2 h

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; aluminum oxide; sodium hydroxide; sodium tetrahydroborate; dipyridinium dichromate; n-butyllithium; diethyl-cyclohexyl-amine; boron trifluoride diethyl etherate; ammonia; dihydrogen peroxide; sodium acetate; lithium; ammonium chloride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; mercury(II) oxide; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide;

Reference yield:

3β,20-dihydroxypregn-5-ene (59042-34-1) → (20R,22R)-3β-t-butyldimethylsilyloxy-5α,20-dihydroxy-6β-phenylthio-1-oxowith-24-enolide (90525-27-2)

Guidance literature:

Multi-step reaction with 16 steps

1: 61 percent / dichlorodicyanobenzoquinone / dioxane / 8 h / Heating

2: toluene-p-sulphonic acid / CH₂Cl₂ / 3 h / Ambient temperature

3: 83 percent / 30percent H₂O₂, NaOH / methanol / 15 °C

4: 1.) liquid NH₃, Li, 2.) NH₄Cl / 1.) THF, -78 deg C -> -40 deg C, 20 min, 2.) 2 h

5: N,N-diethylcyclohexylamine / dioxane / 6 h / Heating

6: 2M HCl / methanol / 2 h / Ambient temperature

7: 80 percent / pyridinium chlorochromate, AcONa / CH₂Cl₂ / 3 h / Ambient temperature

8: 1.) n-BuLi / 1.) THF, - 5 deg C, 2.) -5 deg C, 8 h

9: 85 percent / HgO, BF₃-ether / tetrahydrofuran / 0.5 h / Heating

10: 81 percent / N,N-diethylcyclohexylamine / dioxane / 8 h / Heating

11: 1.) LDA, HMPA / 1.) THF, - 78 deg C, 1 h, 2.) -78 deg C, 6 h

12: 82 percent / 6M HCl / tetrahydrofuran / 3 h / Ambient temperature

13: 90 percent / imidazole / dimethylformamide / 1 h / Ambient temperature

14: 76 percent / m-chloroperbenzoic acid / CHCl₃ / 0.67 h / -5 °C

15: 80 percent / pyridinium dichromate / dimethylformamide / 8 h / -5 °C

16: 1.) alumina Woelm N-20 / 1.) Et₂O, room tempereature, 20 min, 2.) Et₂O-THF, room temperature, 2 h

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; aluminum oxide; sodium hydroxide; dipyridinium dichromate; n-butyllithium; diethyl-cyclohexyl-amine; boron trifluoride diethyl etherate; ammonia; dihydrogen peroxide; sodium acetate; lithium; ammonium chloride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; mercury(II) oxide; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide;

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (20R,22R)-3β-t-butyldimethylsilyloxy-5α,20-dihydroxy-6β-phenylthio-1-oxowith-24-enolide (90525-27-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / imidazole / dimethylformamide / 1 h / Ambient temperature

2: 76 percent / m-chloroperbenzoic acid / CHCl₃ / 0.67 h / -5 °C

3: 80 percent / pyridinium dichromate / dimethylformamide / 8 h / -5 °C

4: 1.) alumina Woelm N-20 / 1.) Et₂O, room tempereature, 20 min, 2.) Et₂O-THF, room temperature, 2 h

With 1H-imidazole; aluminum oxide; dipyridinium dichromate; 3-chloro-benzenecarboperoxoic acid; In chloroform; N,N-dimethyl-formamide;

upstream raw materials:

thiophenol

(20R,22R)-3β-t-butyldimethylsilyloxy-5α,6α-epoxy-20-hydroxy-1-oxowith-24-enolide

Pregnenolone

3β,20-dihydroxypregn-5-ene

Downstream raw materials:

withanolide D

(20R,22R)-20-dihydroxy-6β-phenylthio-1-oxowitha-2,4,24-trienolide

Refernces