(E)-(2S,4R,5S)-10-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-4-(tetrahydro-pyran-2-yloxy)-5-triisopropylsilanyloxy-dec-6-en-1-ol

Base Information

• Chemical Name: (E)-(2S,4R,5S)-10-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-4-(tetrahydro-pyran-2-yloxy)-5-triisopropylsilanyloxy-dec-6-en-1-ol
• CAS No.: 192504-25-9
• Molecular Formula: C₄₁H₆₈O₅Si₂
• Molecular Weight: 697.159
• Mol file: 192504-25-9.mol

Synonyms:

Chemical Property of (E)-(2S,4R,5S)-10-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-4-(tetrahydro-pyran-2-yloxy)-5-triisopropylsilanyloxy-dec-6-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(2S,4R,5S)-10-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-4-(tetrahydro-pyran-2-yloxy)-5-triisopropylsilanyloxy-dec-6-en-1-ol

There total 15 articles about (E)-(2S,4R,5S)-10-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-4-(tetrahydro-pyran-2-yloxy)-5-triisopropylsilanyloxy-dec-6-en-1-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:

Acetic acid (E)-(2S,4R,5S)-10-(tert-butyl-diphenyl-silanyloxy)-2-methyl-4-(tetrahydro-pyran-2-yloxy)-5-triisopropylsilanyloxy-dec-6-enyl ester → (E)-(2S,4R,5S)-10-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-4-(tetrahydro-pyran-2-yloxy)-5-triisopropylsilanyloxy-dec-6-en-1-ol (192504-25-9)

Guidance literature:

With potassium carbonate; In methanol; at 0 - 25 ℃; for 3h; Yield given;

DOI:10.1246/cl.1997.565

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) → (E)-(2S,4R,5S)-10-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-4-(tetrahydro-pyran-2-yloxy)-5-triisopropylsilanyloxy-dec-6-en-1-ol (192504-25-9)

Guidance literature:

Multi-step reaction with 6 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

With 2,6-dimethylpyridine; chromium dichloride; oxalyl dichloride; tetrabutyl ammonium fluoride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 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) → (E)-(2S,4R,5S)-10-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-4-(tetrahydro-pyran-2-yloxy)-5-triisopropylsilanyloxy-dec-6-en-1-ol (192504-25-9)

Guidance literature:

Multi-step reaction with 9 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

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

DOI:10.1246/cl.1997.565

upstream raw materials:

3,4-dihydro-2H-pyran

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

triisopropylsilyl trifluoromethanesulfonate

4-((tert-butyldiphenylsilyl)oxy)butanal

Downstream raw materials:

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

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

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