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

Base Information

• Chemical Name: 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
• CAS No.: 1026062-63-4
• Molecular Formula: C₃₆H₅₀O₅Si
• Molecular Weight: 590.875
• Mol file: 1026062-63-4.mol

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 19 articles about 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 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) → 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 (1026062-63-4)

Guidance literature:

Multi-step reaction with 12 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

10: TBAF / tetrahydrofuran / 12 h / 25 °C

11: imidazole / dimethylformamide / 0.5 h / 0 °C

12: Et₃N, DMAP / CH₂Cl₂ / 0.5 h / 0 °C

With 1H-imidazole; 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; N,N-dimethyl-formamide;

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) → 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 (1026062-63-4)

Guidance literature:

Multi-step reaction with 15 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

13: TBAF / tetrahydrofuran / 12 h / 25 °C

14: imidazole / dimethylformamide / 0.5 h / 0 °C

15: Et₃N, DMAP / CH₂Cl₂ / 0.5 h / 0 °C

With 1H-imidazole; 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; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1246/cl.1997.565

Reference yield:

(4R)-4-Benzyl-3-[(2S)-2-methyl-4-pentenoyl]-1,3-oxazolidin-2-one (175272-36-3) → 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 (1026062-63-4)

Guidance literature:

Multi-step reaction with 16 steps

1: LiBH₄, H₂O / diethyl ether / 0.5 h / 0 °C

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

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

4: Et₃N / CH₂Cl₂ / 12 h / 0 - 25 °C

5: PTSA / CH₂Cl₂ / 2 h / 25 °C

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

7: 94 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1.5 h / -78 - 0 °C

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

9: 2,6-lutidine / CH₂Cl₂ / 0.33 h / 0 °C

10: K₂CO₃ / methanol / 3 h / 0 - 25 °C

11: Et₃N, DMAP / CH₂Cl₂ / 3 h / 25 °C

12: dimethylsulfoxide / 1 h / 90 °C

13: 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

14: TBAF / tetrahydrofuran / 12 h / 25 °C

15: imidazole / dimethylformamide / 0.5 h / 0 °C

16: Et₃N, DMAP / CH₂Cl₂ / 0.5 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; chromium dichloride; dmap; lithium borohydride; oxalyl dichloride; carbon tetrabromide; AD-mix-β; tetrabutyl ammonium fluoride; water; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; nickel dichloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1246/cl.1997.565

upstream raw materials:

3,4-dihydro-2H-pyran

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

tert-butylchlorodiphenylsilane

(4R)-4-Benzyl-3-[(2S)-2-methyl-4-pentenoyl]-1,3-oxazolidin-2-one