2-[(E)-(1R,2S)-7-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2-methyl-pent-4-ynyl)-2-triisopropylsilanyloxy-hept-3-enyloxy]-tetrahydro-pyran

Base Information

• Chemical Name: 2-[(E)-(1R,2S)-7-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2-methyl-pent-4-ynyl)-2-triisopropylsilanyloxy-hept-3-enyloxy]-tetrahydro-pyran
• CAS No.: 192504-27-1
• Molecular Formula: C₄₃H₆₈O₄Si₂
• Molecular Weight: 705.182
• Mol file: 192504-27-1.mol

Synonyms:

Chemical Property of 2-[(E)-(1R,2S)-7-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2-methyl-pent-4-ynyl)-2-triisopropylsilanyloxy-hept-3-enyloxy]-tetrahydro-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(E)-(1R,2S)-7-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2-methyl-pent-4-ynyl)-2-triisopropylsilanyloxy-hept-3-enyloxy]-tetrahydro-pyran

There total 18 articles about 2-[(E)-(1R,2S)-7-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2-methyl-pent-4-ynyl)-2-triisopropylsilanyloxy-hept-3-enyloxy]-tetrahydro-pyran 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:

3,4-dihydro-2H-pyran (110-87-2) → 2-[(E)-(1R,2S)-7-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2-methyl-pent-4-ynyl)-2-triisopropylsilanyloxy-hept-3-enyloxy]-tetrahydro-pyran (192504-27-1)

Guidance literature:

Multi-step reaction with 9 steps

1: PTSA / CH₂Cl₂ / 2 h / 25 °C

2: TBAF / tetrahydrofuran / 6 h / 0 - 25 °C

3: 94 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1.5 h / -78 - 0 °C

4: CrCl₂, NiCl₂ / dimethylsulfoxide / 12 h / 25 °C

5: 2,6-lutidine / CH₂Cl₂ / 0.33 h / 0 °C

6: K₂CO₃ / methanol / 3 h / 0 - 25 °C

7: Et₃N, DMAP / CH₂Cl₂ / 3 h / 25 °C

8: dimethylsulfoxide / 1 h / 90 °C

9: 1.) DIBAL; 2.) Ph₃P, CBr₄, Et₃N / 1.) toluene, -78 deg C, 30 min; 2.) CH₂Cl₂, 0 deg C, 10 min; 3.) THF, 0 deg C to 25 deg C, 30 min

With 2,6-dimethylpyridine; chromium dichloride; dmap; oxalyl dichloride; carbon tetrabromide; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; nickel dichloride; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1246/cl.1997.565

Reference yield:

(S)-(-)-2-methyl-4-penten-1-ol (5673-98-3,63501-27-9,88080-30-2,63501-26-8) → 2-[(E)-(1R,2S)-7-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2-methyl-pent-4-ynyl)-2-triisopropylsilanyloxy-hept-3-enyloxy]-tetrahydro-pyran (192504-27-1)

Guidance literature:

Multi-step reaction with 12 steps

1: Et₃N, DMAP / CH₂Cl₂ / 0.33 h / 0 °C

2: AD-mix-β / 2-methyl-propan-2-ol; H2O / 6 h / 0 °C

3: Et₃N / CH₂Cl₂ / 12 h / 0 - 25 °C

4: PTSA / CH₂Cl₂ / 2 h / 25 °C

5: TBAF / tetrahydrofuran / 6 h / 0 - 25 °C

6: 94 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1.5 h / -78 - 0 °C

7: CrCl₂, NiCl₂ / dimethylsulfoxide / 12 h / 25 °C

8: 2,6-lutidine / CH₂Cl₂ / 0.33 h / 0 °C

9: K₂CO₃ / methanol / 3 h / 0 - 25 °C

10: Et₃N, DMAP / CH₂Cl₂ / 3 h / 25 °C

11: dimethylsulfoxide / 1 h / 90 °C

12: 1.) DIBAL; 2.) Ph₃P, CBr₄, Et₃N / 1.) toluene, -78 deg C, 30 min; 2.) CH₂Cl₂, 0 deg C, 10 min; 3.) THF, 0 deg C to 25 deg C, 30 min

With 2,6-dimethylpyridine; chromium dichloride; dmap; oxalyl dichloride; carbon tetrabromide; AD-mix-β; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; nickel dichloride; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; tert-butyl alcohol;

DOI:10.1246/cl.1997.565

Reference yield:

4-((tert-butyldiphenylsilyl)oxy)butanal (127793-62-8) → 2-[(E)-(1R,2S)-7-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2-methyl-pent-4-ynyl)-2-triisopropylsilanyloxy-hept-3-enyloxy]-tetrahydro-pyran (192504-27-1)

Guidance literature:

Multi-step reaction with 7 steps

1: CrCl₂ / tetrahydrofuran; dioxane

2: CrCl₂, NiCl₂ / dimethylsulfoxide / 12 h / 25 °C

3: 2,6-lutidine / CH₂Cl₂ / 0.33 h / 0 °C

4: K₂CO₃ / methanol / 3 h / 0 - 25 °C

5: Et₃N, DMAP / CH₂Cl₂ / 3 h / 25 °C

6: dimethylsulfoxide / 1 h / 90 °C

7: 1.) DIBAL; 2.) Ph₃P, CBr₄, Et₃N / 1.) toluene, -78 deg C, 30 min; 2.) CH₂Cl₂, 0 deg C, 10 min; 3.) THF, 0 deg C to 25 deg C, 30 min

With 2,6-dimethylpyridine; chromium dichloride; dmap; carbon tetrabromide; diisobutylaluminium hydride; potassium carbonate; triethylamine; triphenylphosphine; nickel dichloride; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1246/cl.1997.565

upstream raw materials:

ethylmagnesium bromide

(E)-(3R,5R,6S)-11-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-5-(tetrahydro-pyran-2-yloxy)-6-triisopropylsilanyloxy-undec-7-enenitrile

3,4-dihydro-2H-pyran

(S)-(-)-2-methyl-4-penten-1-ol

Downstream raw materials:

Acetic acid (1S,2R,4R)-1-[(E)-5-(tert-butyl-diphenyl-silanyloxy)-pent-1-enyl]-4-methyl-2-(tetrahydro-pyran-2-yloxy)-hept-6-ynyl ester