1-Benzyloxy-5-bromo-3-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propyl]-6-methoxy-8-methoxymethoxy-naphthalene-2-carbaldehyde

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Chemical Name:1-Benzyloxy-5-bromo-3-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propyl]-6-methoxy-8-methoxymethoxy-naphthalene-2-carbaldehyde
CAS No.:133363-18-5
Molecular Formula:C₄₀H₄₃BrO₆Si
Molecular Weight:727.767
Hs Code.:

Synonyms:1-Benzyloxy-5-bromo-3-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propyl]-6-methoxy-8-methoxymethoxy-naphthalene-2-carbaldehyde

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Chemical Property of 1-Benzyloxy-5-bromo-3-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propyl]-6-methoxy-8-methoxymethoxy-naphthalene-2-carbaldehyde

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Technology Process of 1-Benzyloxy-5-bromo-3-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propyl]-6-methoxy-8-methoxymethoxy-naphthalene-2-carbaldehyde

There total 14 articles about 1-Benzyloxy-5-bromo-3-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propyl]-6-methoxy-8-methoxymethoxy-naphthalene-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: 91.0%

: 133363-17-4
1-Benzyloxy-3-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propyl]-6-methoxy-8-methoxymethoxy-naphthalene-2-carbaldehyde

: 133363-18-5
1-Benzyloxy-5-bromo-3-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propyl]-6-methoxy-8-methoxymethoxy-naphthalene-2-carbaldehyde

Guidance literature:: With N-Bromosuccinimide; In dichloromethane; at 20 ℃; for 0.5h;
DOI:10.1016/S0040-4039(00)92105-1

Reference yield:

: 13321-73-8
2-bromo-1,5-dimethoxy-3-methylbenzene

: 133363-18-5
1-Benzyloxy-5-bromo-3-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propyl]-6-methoxy-8-methoxymethoxy-naphthalene-2-carbaldehyde

Guidance literature:: Multi-step reaction with 14 steps

1: 1.) n-BuLi / 1.) Et₂O, 0 deg, 30 min

2: (COCl)2 / 0 - 20 °C

3: pyridine

4: BBr₃ / CH₂Cl₂ / 0.5 h / 0 °C

5: NaH / dimethylformamide

6: 1.) LDA / 1.) THF, -78 deg, 10 min

7: DDQ / dioxane / 0.17 h / 60 °C

8: K₂CO₃ / dimethylsulfoxide / 16 h / 20 °C

9: LAH / tetrahydrofuran / 1 h / 0 °C

10: pyridine / 24 h

11: imidazole / dimethylformamide / 16 h / 0 - 20 °C

12: TsOH / CH₂Cl₂; methanol / 0.08 h

13: 62 percent / PCC / CH₂Cl₂ / 20 °C

14: 91 percent / NBS / CH₂Cl₂ / 0.5 h / 20 °C

With pyridine; 1H-imidazole; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; boron tribromide; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)92105-1

Reference yield:

: 3686-57-5
2,4-dimethoxy-6-methylbenzoic acid

: 133363-18-5
1-Benzyloxy-5-bromo-3-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propyl]-6-methoxy-8-methoxymethoxy-naphthalene-2-carbaldehyde

Guidance literature:: Multi-step reaction with 13 steps

1: (COCl)2 / 0 - 20 °C

2: pyridine

3: BBr₃ / CH₂Cl₂ / 0.5 h / 0 °C

4: NaH / dimethylformamide

5: 1.) LDA / 1.) THF, -78 deg, 10 min

6: DDQ / dioxane / 0.17 h / 60 °C

7: K₂CO₃ / dimethylsulfoxide / 16 h / 20 °C

8: LAH / tetrahydrofuran / 1 h / 0 °C

9: pyridine / 24 h

10: imidazole / dimethylformamide / 16 h / 0 - 20 °C

11: TsOH / CH₂Cl₂; methanol / 0.08 h

12: 62 percent / PCC / CH₂Cl₂ / 20 °C

13: 91 percent / NBS / CH₂Cl₂ / 0.5 h / 20 °C

With pyridine; 1H-imidazole; N-Bromosuccinimide; lithium aluminium tetrahydride; oxalyl dichloride; boron tribromide; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)92105-1