[4-(tert-Butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-naphthalen-2-yl]-methyl-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [4-(tert-Butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-naphthalen-2-yl]-methyl-carbamic acid tert-butyl ester
• CAS No.: 157528-28-4
• Molecular Formula: C₄₉H₅₇NO₄Si₂
• Molecular Weight: 780.167
• Mol file: 157528-28-4.mol

Synonyms:[4-(tert-Butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-naphthalen-2-yl]-methyl-carbamic acid tert-butyl ester

Chemical Property of [4-(tert-Butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-naphthalen-2-yl]-methyl-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [4-(tert-Butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-naphthalen-2-yl]-methyl-carbamic acid tert-butyl ester

There total 9 articles about [4-(tert-Butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-naphthalen-2-yl]-methyl-carbamic acid tert-butyl 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: 43.0%

tert-butylchlorodiphenylsilane (58479-61-1) + 3--4-(hydroxymethyl)-1-naphthol (157528-15-9) → [4-(tert-Butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-naphthalen-2-yl]-methyl-carbamic acid tert-butyl ester (157528-28-4)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 100 ℃; for 1h;

DOI:10.1021/jo00096a043

Reference yield:

2-((tert-Butyloxycarbonyl)amino)-4-(benzyloxy)-1-bromonaphthalene (122745-37-3) → [4-(tert-Butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-naphthalen-2-yl]-methyl-carbamic acid tert-butyl ester (157528-28-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 94 percent / NaH / dimethylformamide / 1.) 25 deg C, 30 min, 2.) 25 deg C, 2 h

2: 1.) n-BuLi, 2.) H₂ / 2.) 10percent Pd-C

3: 91 percent / DMAP / dioxane / 1 h / 100 °C

4: 76 percent / NaBH₄ / ethanol / 0.5 h / 25 °C

5: 43 percent / imidazole / dimethylformamide / 1 h / 100 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; n-butyllithium; hydrogen; sodium hydride; palladium on activated charcoal; In 1,4-dioxane; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jo00096a043

Reference yield:

N-(tert-butyloxycarbonyl)-4-(benzyloxy)-2-naphthylamine (122745-36-2) → [4-(tert-Butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-naphthalen-2-yl]-methyl-carbamic acid tert-butyl ester (157528-28-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 97 percent / conc. H₂SO₄, NBS / tetrahydrofuran / 1.) -78 deg C, 5 min, 2.) -78 deg C, 5 h

2: 94 percent / NaH / dimethylformamide / 1.) 25 deg C, 30 min, 2.) 25 deg C, 2 h

3: 1.) n-BuLi, 2.) H₂ / 2.) 10percent Pd-C

4: 91 percent / DMAP / dioxane / 1 h / 100 °C

5: 76 percent / NaBH₄ / ethanol / 0.5 h / 25 °C

6: 43 percent / imidazole / dimethylformamide / 1 h / 100 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; N-Bromosuccinimide; n-butyllithium; sulfuric acid; hydrogen; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jo00096a043

upstream raw materials:

tert-butylchlorodiphenylsilane

3--4-(hydroxymethyl)-1-naphthol

di-tert-butyl dicarbonate

N-(tert-butyloxycarbonyl)-4-(benzyloxy)-2-naphthylamine

Downstream raw materials:

6-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-1,4-dihydro-naphtho[2,1-d][1,3]oxazin-3-one

2-(methylamino)-1,4-naphthoquinone