(9S,10S)-11-(tert-Butyl-diphenyl-silanyloxy)-9-hydroxy-10-methyl-undec-1-en-5-one

Base Information

• Chemical Name: (9S,10S)-11-(tert-Butyl-diphenyl-silanyloxy)-9-hydroxy-10-methyl-undec-1-en-5-one
• CAS No.: 786668-29-9
• Molecular Formula: C₂₈H₄₀O₃Si
• Molecular Weight: 452.709
• Mol file: 786668-29-9.mol

Synonyms:(9S,10S)-11-(tert-Butyl-diphenyl-silanyloxy)-9-hydroxy-10-methyl-undec-1-en-5-one

Chemical Property of (9S,10S)-11-(tert-Butyl-diphenyl-silanyloxy)-9-hydroxy-10-methyl-undec-1-en-5-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (9S,10S)-11-(tert-Butyl-diphenyl-silanyloxy)-9-hydroxy-10-methyl-undec-1-en-5-one

There total 10 articles about (9S,10S)-11-(tert-Butyl-diphenyl-silanyloxy)-9-hydroxy-10-methyl-undec-1-en-5-one 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:

1 ,5-pentanediol (111-29-5) → (9S,10S)-11-(tert-Butyl-diphenyl-silanyloxy)-9-hydroxy-10-methyl-undec-1-en-5-one (786668-29-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 80 percent / KOH / 4 h / 20 °C

2.1: 93 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -55 - 20 °C

3.1: NaI; NaH / tetrahydrofuran / 8 h / -78 °C

4.1: 94 percent / DIBALH / tetrahydrofuran; toluene / -78 - 0 °C

5.1: (-)-D-diethyl tartrate; ti(OiPr)4; tert-butyl hydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 70 h / -20 °C

6.1: CuCN / diethyl ether / 1 h / -20 °C

6.2: diethyl ether / 2.5 h / -15 °C

6.3: 65 percent / NaIO₄ / tetrahydrofuran; H₂O / 1.5 h / 20 °C

7.1: 98 percent / Et₃N / CH₂Cl₂ / 14 h / 20 °C

8.1: 89 percent / H₂ / Pd(OH)2/C / ethyl acetate / 13 h / 20 °C

9.1: 58 percent / pyridinium chlorochromate / CH₂Cl₂ / 21 h / 20 °C

10.1: Mg / tetrahydrofuran / 0.83 h

10.2: 60 percent / tetrahydrofuran / 0.67 h / -78 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; potassium hydroxide; oxalyl dichloride; diethyl (2S,3S)-tartrate; hydrogen; sodium hydride; diisobutylaluminium hydride; magnesium; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; sodium iodide; palladium dihydroxide; In tetrahydrofuran; 2,2,4-trimethylpentane; diethyl ether; dichloromethane; ethyl acetate; toluene; 2.1: Swern oxidation / 3.1: Horner-Wadsworth-Emmons olefination / 5.1: Katsuki-Sharpless asymmetric epoxidation;

DOI:10.1021/ol048321t

Reference yield:

5-(benzyloxy)-1-pentanol (4541-15-5) → (9S,10S)-11-(tert-Butyl-diphenyl-silanyloxy)-9-hydroxy-10-methyl-undec-1-en-5-one (786668-29-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 93 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -55 - 20 °C

2.1: NaI; NaH / tetrahydrofuran / 8 h / -78 °C

3.1: 94 percent / DIBALH / tetrahydrofuran; toluene / -78 - 0 °C

4.1: (-)-D-diethyl tartrate; ti(OiPr)4; tert-butyl hydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 70 h / -20 °C

5.1: CuCN / diethyl ether / 1 h / -20 °C

5.2: diethyl ether / 2.5 h / -15 °C

5.3: 65 percent / NaIO₄ / tetrahydrofuran; H₂O / 1.5 h / 20 °C

6.1: 98 percent / Et₃N / CH₂Cl₂ / 14 h / 20 °C

7.1: 89 percent / H₂ / Pd(OH)2/C / ethyl acetate / 13 h / 20 °C

8.1: 58 percent / pyridinium chlorochromate / CH₂Cl₂ / 21 h / 20 °C

9.1: Mg / tetrahydrofuran / 0.83 h

9.2: 60 percent / tetrahydrofuran / 0.67 h / -78 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; diethyl (2S,3S)-tartrate; hydrogen; sodium hydride; diisobutylaluminium hydride; magnesium; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; sodium iodide; palladium dihydroxide; In tetrahydrofuran; 2,2,4-trimethylpentane; diethyl ether; dichloromethane; ethyl acetate; toluene; 1.1: Swern oxidation / 2.1: Horner-Wadsworth-Emmons olefination / 4.1: Katsuki-Sharpless asymmetric epoxidation;

DOI:10.1021/ol048321t

Reference yield:

5-benzyloxy-1-pentanal (78999-24-3) → (9S,10S)-11-(tert-Butyl-diphenyl-silanyloxy)-9-hydroxy-10-methyl-undec-1-en-5-one (786668-29-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: NaI; NaH / tetrahydrofuran / 8 h / -78 °C

2.1: 94 percent / DIBALH / tetrahydrofuran; toluene / -78 - 0 °C

3.1: (-)-D-diethyl tartrate; ti(OiPr)4; tert-butyl hydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 70 h / -20 °C

4.1: CuCN / diethyl ether / 1 h / -20 °C

4.2: diethyl ether / 2.5 h / -15 °C

4.3: 65 percent / NaIO₄ / tetrahydrofuran; H₂O / 1.5 h / 20 °C

5.1: 98 percent / Et₃N / CH₂Cl₂ / 14 h / 20 °C

6.1: 89 percent / H₂ / Pd(OH)2/C / ethyl acetate / 13 h / 20 °C

7.1: 58 percent / pyridinium chlorochromate / CH₂Cl₂ / 21 h / 20 °C

8.1: Mg / tetrahydrofuran / 0.83 h

8.2: 60 percent / tetrahydrofuran / 0.67 h / -78 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate; hydrogen; sodium hydride; diisobutylaluminium hydride; magnesium; triethylamine; pyridinium chlorochromate; sodium iodide; palladium dihydroxide; In tetrahydrofuran; 2,2,4-trimethylpentane; diethyl ether; dichloromethane; ethyl acetate; toluene; 1.1: Horner-Wadsworth-Emmons olefination / 3.1: Katsuki-Sharpless asymmetric epoxidation;

DOI:10.1021/ol048321t

upstream raw materials:

1 ,5-pentanediol

5-(benzyloxy)-1-pentanol

5-benzyloxy-1-pentanal

(Z)-7-(benzyloxy)hept-2-en-1-ol

Downstream raw materials:

{(S)-2-[(2S,6R)-6-But-3-enyl-6-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-propoxy}-tert-butyl-diphenyl-silane