(5E,7E,20S)-3β-(tert-butyldimethylsilyloxy)-20-(p-tolylsulfonyloxymethyl)-9,10-seco-5,7,10(19)-pregnatriene

Base Information

• Chemical Name: (5E,7E,20S)-3β-(tert-butyldimethylsilyloxy)-20-(p-tolylsulfonyloxymethyl)-9,10-seco-5,7,10(19)-pregnatriene
• CAS No.: 143884-24-6
• Molecular Formula: C₃₅H₅₄O₄SSi
• Molecular Weight: 598.963
• Mol file: 143884-24-6.mol

Synonyms:(5E,7E,20S)-3β-(tert-butyldimethylsilyloxy)-20-(p-tolylsulfonyloxymethyl)-9,10-seco-5,7,10(19)-pregnatriene

Chemical Property of (5E,7E,20S)-3β-(tert-butyldimethylsilyloxy)-20-(p-tolylsulfonyloxymethyl)-9,10-seco-5,7,10(19)-pregnatriene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5E,7E,20S)-3β-(tert-butyldimethylsilyloxy)-20-(p-tolylsulfonyloxymethyl)-9,10-seco-5,7,10(19)-pregnatriene

There total 8 articles about (5E,7E,20S)-3β-(tert-butyldimethylsilyloxy)-20-(p-tolylsulfonyloxymethyl)-9,10-seco-5,7,10(19)-pregnatriene 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:

Toluene-4-sulfonic acid (S)-2-{(R)-4-[1-[(S)-6-(tert-butyl-dimethyl-silanyloxy)-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2λ6-benzo[c]thiophen-1-yl]-meth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl ester → Toluene-4-sulfonic acid (S)-2-{(R)-4-[2-[(S)-5-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl ester (143884-24-6)

Guidance literature:

With sodium hydrogencarbonate; In ethanol; Yield given; Heating;

DOI:10.1248/cpb.40.1662

Reference yield:

Toluene-4-sulfonic acid (S)-2-{(1R,3aS,7aR)-4-[1-[(S)-6-(tert-butyl-dimethyl-silanyloxy)-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2λ6-benzo[c]thiophen-1-yl]-meth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl ester → (5E,7E,20S)-3β-(tert-butyldimethylsilyloxy)-20-(p-tolylsulfonyloxymethyl)-9,10-seco-5,7,10(19)-pregnatriene (143884-24-6)

Guidance literature:

With sodium hydrogencarbonate; In ethanol; for 1h; Yield given; Heating;

DOI:10.1248/cpb.43.189

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → Toluene-4-sulfonic acid (S)-2-{(R)-4-[2-[(S)-5-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl ester (143884-24-6)

Guidance literature:

Multi-step reaction with 5 steps

1: imidazole / dimethylformamide

2: O₃, pyridine / methanol; CH₂Cl₂ / -78 °C

3: NaBH₄ / methanol / 0 °C

4: pyridine / 5 °C

5: NaHCO₃ / ethanol / Heating

With pyridine; 1H-imidazole; sodium tetrahydroborate; sodium hydrogencarbonate; ozone; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.40.1662

upstream raw materials:

tert-butyldimethylsilyl chloride

vitamin D₂

(S)-3-[(R)-7a-Methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-(4E)-ylidenemethyl]-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2λ⁶-benzo[c]thiophen-5-ol

(S)-2-{(R)-4-[1-[(S)-6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2λ⁶-benzo[c]thiophen-1-yl]-meth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propan-1-ol

Downstream raw materials:

Toluene-4-sulfonic acid (S)-2-{(R)-4-[2-[(3S,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl ester

Toluene-4-sulfonic acid (S)-2-{(R)-4-[2-[(3R,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl ester

Toluene-4-sulfonic acid (S)-2-{(R)-4-[2-[(3R,5R)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2-methylene-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl ester

Toluene-4-sulfonic acid (S)-2-{(R)-4-[2-[(3S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2-methylene-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl ester