(S)-2-[(1R,3aS,7aR,E)-4-((E)-2-{(3S,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-2-methylenecyclohexylidene}ethylidene)-7a-methyloctahydro-1H-inden-1-yl]propyl 4-methylbenzenesulfonate

Base Information

• Chemical Name: (S)-2-[(1R,3aS,7aR,E)-4-((E)-2-{(3S,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-2-methylenecyclohexylidene}ethylidene)-7a-methyloctahydro-1H-inden-1-yl]propyl 4-methylbenzenesulfonate
• CAS No.: 128387-36-0
• Molecular Formula: C₄₁H₆₈O₅SSi₂
• Molecular Weight: 729.225
• Mol file: 128387-36-0.mol

Synonyms:(S)-2-[(1R,3aS,7aR,E)-4-((E)-2-{(3S,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-2-methylenecyclohexylidene}ethylidene)-7a-methyloctahydro-1H-inden-1-yl]propyl 4-methylbenzenesulfonate

Chemical Property of (S)-2-[(1R,3aS,7aR,E)-4-((E)-2-{(3S,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-2-methylenecyclohexylidene}ethylidene)-7a-methyloctahydro-1H-inden-1-yl]propyl 4-methylbenzenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-[(1R,3aS,7aR,E)-4-((E)-2-{(3S,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-2-methylenecyclohexylidene}ethylidene)-7a-methyloctahydro-1H-inden-1-yl]propyl 4-methylbenzenesulfonate

There total 12 articles about (S)-2-[(1R,3aS,7aR,E)-4-((E)-2-{(3S,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-2-methylenecyclohexylidene}ethylidene)-7a-methyloctahydro-1H-inden-1-yl]propyl 4-methylbenzenesulfonate 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: 92.0%

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 (114694-13-2,128387-36-0,134523-95-8) → Toluene-4-sulfonic acid (S)-2-{(R)-4-[2-[(3S,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl ester (114694-13-2,128387-36-0,134523-95-8)

Guidance literature:

With anthracene; triethylamine; In toluene; at 0 ℃; Irradiation;

DOI:10.1248/cpb.40.1662

Reference yield: 91.0%

p-toluenesulfonyl chloride (98-59-9) + (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(S)-(hydroxymethyl)-9,10-secopregna-5(E),7(E),10(19)-triene (128387-35-9) → (S)-2-[(1R,3aS,7aR,E)-4-((E)-2-{(3S,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-2-methylenecyclohexylidene}ethylidene)-7a-methyloctahydro-1H-inden-1-yl]propyl 4-methylbenzenesulfonate (128387-36-0)

Guidance literature:

With pyridine; dmap;

DOI:10.1016/j.tetlet.2007.07.086

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 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 (114694-13-2,128387-36-0,134523-95-8)

Guidance literature:

Multi-step reaction with 6 steps

1: imidazole / dimethylformamide

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

3: NaBH₄ / methanol / 0 °C

4: pyridine / 5 °C

5: NaHCO₃ / ethanol / Heating

6: 1.) SeO₂-NMO, 2.) imidazole / 1.) MeOH, CH₂Cl₂, reflux, 2.) DMF

With pyridine; 1H-imidazole; sodium tetrahydroborate; selenium(IV) oxide; sodium hydrogencarbonate; ozone; 4-methylmorpholine N-oxide; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.40.1662

upstream 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

tert-butyldimethylsilyl chloride

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

vitamin D₂

Downstream raw materials:

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

C₃₆H₆₄O₃Si₂S

ethyl 2-{(S)-2-[(1R,3aS,7aR,E)-4-((E)-2-{(3S,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-2-methylenecyclohexylidene}ethylidene)-7a-methyloctahydro-1H-inden-1-yl]propyl}-2H-tetrazole-5-carboxylate

ethyl 1-{(S)-2-[(1R,3aS,7aR,E)-4-((E)-2-{(3S,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-2-methylenecyclohexylidene}ethylidene)-7a-methyloctahydro-1H-inden-1-yl]propyl}-1H-tetrazole-5-carboxylate