4'-(tert-butyldiphenylsilanyloxymethyl)-6-methoxy-4,2',6'-tris-(4-methoxybenzyloxy)-biphenyl-2-carbaldehyde

Base Information

• Chemical Name: 4'-(tert-butyldiphenylsilanyloxymethyl)-6-methoxy-4,2',6'-tris-(4-methoxybenzyloxy)-biphenyl-2-carbaldehyde
• CAS No.: 444119-60-2
• Molecular Formula: C₅₅H₅₆O₉Si
• Molecular Weight: 889.13

Synonyms:4'-(tert-butyldiphenylsilanyloxymethyl)-6-methoxy-4,2',6'-tris-(4-methoxybenzyloxy)-biphenyl-2-carbaldehyde

Chemical Property of 4'-(tert-butyldiphenylsilanyloxymethyl)-6-methoxy-4,2',6'-tris-(4-methoxybenzyloxy)-biphenyl-2-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 4'-(tert-butyldiphenylsilanyloxymethyl)-6-methoxy-4,2',6'-tris-(4-methoxybenzyloxy)-biphenyl-2-carbaldehyde

There total 14 articles about 4'-(tert-butyldiphenylsilanyloxymethyl)-6-methoxy-4,2',6'-tris-(4-methoxybenzyloxy)-biphenyl-2-carbaldehyde 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: 70.0%

2-[4'-(tert-butyldiphenylsilanyloxymethyl)-6-methoxy-4,2',6'-tris-(4-methoxybenzyloxy)-biphenyl-2-yl]-4,4-dimethyl-4,5-dihydro-oxazole (444119-59-9) → 4'-(tert-butyldiphenylsilanyloxymethyl)-6-methoxy-4,2',6'-tris-(4-methoxybenzyloxy)-biphenyl-2-carbaldehyde (444119-60-2)

Guidance literature:

2-[4'-(tert-butyldiphenylsilanyloxymethyl)-6-methoxy-4,2',6'-tris-(4-methoxybenzyloxy)-biphenyl-2-yl]-4,4-dimethyl-4,5-dihydro-oxazole; With methyl trifluoromethanesulfonate; In dichloromethane; at -10 - 0 ℃; for 2h;

With sodium tetrahydroborate; In tetrahydrofuran; methanol; dichloromethane; at 20 ℃; for 3h;

With oxalic acid; In tetrahydrofuran; for 12h;

DOI:10.1002/1521-3765(20020415)8:8<1850::AID-CHEM1850>3.0.CO;2-Q

Reference yield:

5-bromo-4-hydroxy-3-methoxybenzaldehyde (2973-76-4) → 4'-(tert-butyldiphenylsilanyloxymethyl)-6-methoxy-4,2',6'-tris-(4-methoxybenzyloxy)-biphenyl-2-carbaldehyde (444119-60-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 97 percent / K₂CO₃ / dimethylformamide / 24 h / 20 °C

2.1: 70 percent / 3-chloroperbenzoic acid / CH₂Cl₂ / 16 h / Heating

3.1: 89 percent / dimethylformamide / 12 h / Heating

4.1: 82 percent / K₂CO₃; n-Bu₄NI / dimethylformamide / 12 h / 80 °C

5.1: 98 percent / aq. LiOH / methanol / 72 h / Heating

6.1: 80 percent / PPh₃; (iPr)2NEt; CCl₄ / pyridine; acetonitrile / 16 h / 80 °C

7.1: Mg; 1,2-dibromoethane / tetrahydrofuran / 3 h / Heating

7.2: 84 percent / tetrahydrofuran / 48 h / Heating

8.1: methyl triflate / CH₂Cl₂ / 2 h / -10 - 0 °C

8.2: NaBH₄ / methanol; tetrahydrofuran; CH₂Cl₂ / 3 h / 20 °C

8.3: 70 percent / aq. oxalic acid / tetrahydrofuran / 12 h

With tetrachloromethane; lithium hydroxide; tetra-(n-butyl)ammonium iodide; potassium carbonate; magnesium; ethylene dibromide; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; methyl trifluoromethanesulfonate; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 2.1: Baeyer-Villiger oxidation;

DOI:10.1002/1521-3765(20020415)8:8<1850::AID-CHEM1850>3.0.CO;2-Q

Reference yield:

3,5-dihydroxy-4-bromobenzoic acid (16534-12-6) → 4'-(tert-butyldiphenylsilanyloxymethyl)-6-methoxy-4,2',6'-tris-(4-methoxybenzyloxy)-biphenyl-2-carbaldehyde (444119-60-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 96 percent / SOCl₂ / 2 h / Heating

2.1: 84 percent / K₂CO₃; nBu₄NI / dimethylformamide / 12 h / 80 °C

3.1: 98 percent / LiBH₄ / tetrahydrofuran; methanol / 3 h / Heating

4.1: 82 percent / imidazole / dimethylformamide / 12 h / 20 °C

5.1: Mg; 1,2-dibromoethane / tetrahydrofuran / 3 h / Heating

5.2: 84 percent / tetrahydrofuran / 48 h / Heating

6.1: methyl triflate / CH₂Cl₂ / 2 h / -10 - 0 °C

6.2: NaBH₄ / methanol; tetrahydrofuran; CH₂Cl₂ / 3 h / 20 °C

6.3: 70 percent / aq. oxalic acid / tetrahydrofuran / 12 h

With 1H-imidazole; lithium borohydride; thionyl chloride; tetra-(n-butyl)ammonium iodide; potassium carbonate; magnesium; ethylene dibromide; methyl trifluoromethanesulfonate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/1521-3765(20020415)8:8<1850::AID-CHEM1850>3.0.CO;2-Q

upstream raw materials:

2-[4'-(tert-butyldiphenylsilanyloxymethyl)-6-methoxy-4,2',6'-tris-(4-methoxybenzyloxy)-biphenyl-2-yl]-4,4-dimethyl-4,5-dihydro-oxazole

5-bromo-4-hydroxy-3-methoxybenzaldehyde

3,5-dihydroxy-4-bromobenzoic acid

5-bromoveratralaldehyde

Downstream raw materials:

1-[4'-(tert-butyldiphenylsilanyloxymethyl)-6-methoxy-4,2',6'-tris-(4-methoxybenzyloxy)-biphenyl-2-yl]-pent-4-en-1-ol

1-[4'-(tert-butyldiphenylsilanyloxymethyl)-6-methoxy-4,2',6'-tris-(4-methoxybenzyloxy)-biphenyl-2-yl]-hex-4-yn-1-ol

thiocarbonic acid O-{1-[4'-(tert-butyldiphenylsilanyloxymethyl)-6-methoxy-4,2',6'-tris-(4-methoxybenzyloxy)-biphenyl-2-yl]-oct-6-ynyl} ester O-phenyl ester

thiocarbonic acid O-{1-[4'-(tert-butyldiphenylsilanyloxymethyl)-6-methoxy-4,2',6'-tris-(4-methoxybenzyloxy)-biphenyl-2-yl]-hept-6-enyl} ester O-phenyl ester

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