1-benzyloxy-11,15-bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-3-methyl-13-triethylsilanyloxy-hexadeca-2,8-dien-7-one

Base Information

• Chemical Name: 1-benzyloxy-11,15-bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-3-methyl-13-triethylsilanyloxy-hexadeca-2,8-dien-7-one
• CAS No.: 916757-70-5
• Molecular Formula: C₄₂H₇₈O₆Si₃
• Molecular Weight: 763.334

Synonyms:1-benzyloxy-11,15-bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-3-methyl-13-triethylsilanyloxy-hexadeca-2,8-dien-7-one

Chemical Property of 1-benzyloxy-11,15-bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-3-methyl-13-triethylsilanyloxy-hexadeca-2,8-dien-7-one

Chemical Property:

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Technology Process of 1-benzyloxy-11,15-bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-3-methyl-13-triethylsilanyloxy-hexadeca-2,8-dien-7-one

There total 24 articles about 1-benzyloxy-11,15-bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-3-methyl-13-triethylsilanyloxy-hexadeca-2,8-dien-7-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:

5,7-bis-(tert-butyl-dimethyl-silanyloxy)-3-iodo-hept-2-en-1-ol (916757-65-8) → 1-benzyloxy-11,15-bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-3-methyl-13-triethylsilanyloxy-hexadeca-2,8-dien-7-one (916757-70-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: triethylamine / tetrahydrofuran / 2 h / 25 °C

2.1: Pd(bis-(diphenylphosphino)ferrocene)Cl₂ / tetrahydrofuran; toluene / 12 h / 65 °C

3.1: 19.2 g / K₂CO₃ / methanol / 4 h / 25 °C

4.1: 88 percent / NaH; n-Bu₄NI / tetrahydrofuran / 6 h / 25 °C

5.1: 9 percent / HF*Py / tetrahydrofuran / 3 h / 0 °C

6.1: 73 percent / NaHCO₃; pyridinium chlorochromate / CH₂Cl₂ / 3 h / 25 °C

7.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 °C

7.2: tetrahydrofuran; hexane / 2 h / -78 °C

8.1: 11.1 g / pyridinium dichromate / dimethylformamide / 12 h / 25 °C

9.1: 92 percent / aq. HF / acetonitrile / 3 h / 25 °C

10.1: 95 percent / Ba(OH)2*H₂O / tetrahydrofuran; H₂O / 1 h / 25 °C

With barium dihydroxide; dipyridinium dichromate; n-butyllithium; hydrogen fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; pyridine hydrogenfluoride; triethylamine; pyridinium chlorochromate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 2.1: Negishi coupling / 10.1: Horner-Wadsworth-Emmons olefination;

DOI:10.1021/ja068053p

Reference yield:

1-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-hept-5-yn-3-ol (916757-63-6) → 1-benzyloxy-11,15-bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-3-methyl-13-triethylsilanyloxy-hexadeca-2,8-dien-7-one (916757-70-5)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 96 percent / imidazole / dimethylformamide / 6 h / 25 °C

2.1: 79 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; aq. phosphate buffer / 3 h / 25 °C / pH 7

3.1: Red-Al / tetrahydrofuran; toluene / 0.75 h / 25 °C

3.2: 66 percent / N-iodosuccinimide / tetrahydrofuran; toluene / 0.5 h / -78 °C

4.1: triethylamine / tetrahydrofuran / 2 h / 25 °C

5.1: Pd(bis-(diphenylphosphino)ferrocene)Cl₂ / tetrahydrofuran; toluene / 12 h / 65 °C

6.1: 19.2 g / K₂CO₃ / methanol / 4 h / 25 °C

7.1: 88 percent / NaH; n-Bu₄NI / tetrahydrofuran / 6 h / 25 °C

8.1: 9 percent / HF*Py / tetrahydrofuran / 3 h / 0 °C

9.1: 73 percent / NaHCO₃; pyridinium chlorochromate / CH₂Cl₂ / 3 h / 25 °C

10.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 °C

10.2: tetrahydrofuran; hexane / 2 h / -78 °C

11.1: 11.1 g / pyridinium dichromate / dimethylformamide / 12 h / 25 °C

12.1: 92 percent / aq. HF / acetonitrile / 3 h / 25 °C

13.1: 95 percent / Ba(OH)2*H₂O / tetrahydrofuran; H₂O / 1 h / 25 °C

With 1H-imidazole; barium dihydroxide; dipyridinium dichromate; n-butyllithium; hydrogen fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; pyridine hydrogenfluoride; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; methanol; phosphate buffer; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 5.1: Negishi coupling / 13.1: Horner-Wadsworth-Emmons olefination;

DOI:10.1021/ja068053p

Reference yield:

5,7-bis-(tert-butyl-dimethyl-silanyloxy)-hept-2-yn-1-ol (916757-46-5) → 1-benzyloxy-11,15-bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-3-methyl-13-triethylsilanyloxy-hexadeca-2,8-dien-7-one (916757-70-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: Red-Al / tetrahydrofuran; toluene / 0.75 h / 25 °C

1.2: 66 percent / N-iodosuccinimide / tetrahydrofuran; toluene / 0.5 h / -78 °C

2.1: triethylamine / tetrahydrofuran / 2 h / 25 °C

3.1: Pd(bis-(diphenylphosphino)ferrocene)Cl₂ / tetrahydrofuran; toluene / 12 h / 65 °C

4.1: 19.2 g / K₂CO₃ / methanol / 4 h / 25 °C

5.1: 88 percent / NaH; n-Bu₄NI / tetrahydrofuran / 6 h / 25 °C

6.1: 9 percent / HF*Py / tetrahydrofuran / 3 h / 0 °C

7.1: 73 percent / NaHCO₃; pyridinium chlorochromate / CH₂Cl₂ / 3 h / 25 °C

8.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 °C

8.2: tetrahydrofuran; hexane / 2 h / -78 °C

9.1: 11.1 g / pyridinium dichromate / dimethylformamide / 12 h / 25 °C

10.1: 92 percent / aq. HF / acetonitrile / 3 h / 25 °C

11.1: 95 percent / Ba(OH)2*H₂O / tetrahydrofuran; H₂O / 1 h / 25 °C

With barium dihydroxide; dipyridinium dichromate; n-butyllithium; hydrogen fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; pyridine hydrogenfluoride; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; pyridinium chlorochromate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 3.1: Negishi coupling / 11.1: Horner-Wadsworth-Emmons olefination;

DOI:10.1021/ja068053p

upstream raw materials:

7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hept-5-enal

7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hept-5-en-1-ol

5,7-bis-(tert-butyl-dimethyl-silanyloxy)-3-methyl-hept-2-en-1-ol

5,7-bis-(tert-butyl-dimethyl-silanyloxy)-hept-2-yn-1-ol

Downstream raw materials:

1-benzyloxy-11,15-bis-(tert-butyl-dimethyl-silanyloxy)-3-methyl-13-triethylsilanyloxy-hexadeca-2,8-diene-5,7-diol

[5,7,11,15-tetrakis-(tert-butyl-dimethyl-silanyloxy)-3-methyl-13-triethylsilanyloxy-hexadeca-2,8-dienyloxymethyl]-benzene

2-acetoxy-6-(4-bromo-buta-1,3-dienyl)-benzoic acid 3,7,9-tris-(tert-butyl-dimethyl-silanyloxy)-1-[2-(tert-butyl-dimethyl-silanyloxy)-propyl]-11-methyl-tetradeca-5,11-dien-13-ynyl ester

2-(4-bromo-buta-1,3-dienyl)-6-triisopropylsilanyloxy-benzoic acid 3,7,9-tris-(tert-butyl-dimethyl-silanyloxy)-1-[2-(tert-butyl-dimethyl-silanyloxy)-propyl]-11-methyl-tetradeca-5,11-dien-13-ynyl ester

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