5,5'-Bis-benzyloxy-7,7'-bis-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propyl]-2,6,2',6'-tetramethoxy-4,4'-bis-methoxymethoxy-[1,1']binaphthalenyl

Base Information

• Chemical Name: 5,5'-Bis-benzyloxy-7,7'-bis-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propyl]-2,6,2',6'-tetramethoxy-4,4'-bis-methoxymethoxy-[1,1']binaphthalenyl
• CAS No.: 133363-21-0
• Molecular Formula: C₈₀H₉₀O₁₂Si₂
• Molecular Weight: 1299.76

Synonyms:

Chemical Property of 5,5'-Bis-benzyloxy-7,7'-bis-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propyl]-2,6,2',6'-tetramethoxy-4,4'-bis-methoxymethoxy-[1,1']binaphthalenyl

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5,5'-Bis-benzyloxy-7,7'-bis-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propyl]-2,6,2',6'-tetramethoxy-4,4'-bis-methoxymethoxy-[1,1']binaphthalenyl

There total 82 articles about 5,5'-Bis-benzyloxy-7,7'-bis-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propyl]-2,6,2',6'-tetramethoxy-4,4'-bis-methoxymethoxy-[1,1']binaphthalenyl 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:

2-bromo-1,5-dimethoxy-3-methylbenzene (13321-73-8) → 5,5'-Bis-benzyloxy-7,7'-bis-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-propyl]-2,6,2',6'-tetramethoxy-4,4'-bis-methoxymethoxy-[1,1']binaphthalenyl (133363-21-0,133443-05-7,133443-06-8,133443-07-9)

Guidance literature:

Multi-step reaction with 22 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

15: MCPBA, Na₂SO₄, 4,4'-methylenebis(2,6-di-t-butyl)phenol / benzene / 1 h / 20 °C

16: aq. NaOH / methanol; tetrahydrofuran / 20 °C

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

18: TBAF

19: DEAD, PPh₃

20: NaOH

22: 1.) t-BuLi, 2.) FeCl₃ / 1.) THF, -78 deg, 2.) -78 deg to 20 deg

With pyridine; 1H-imidazole; sodium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; 4,4'-Methylenebis(2,6-di-tert-butylphenol); tetrabutyl ammonium fluoride; tert.-butyl lithium; boron tribromide; iron(III) chloride; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; sodium sulfate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4039(00)92105-1

Reference yield:

2-bromo-1,5-dimethoxy-3-methylbenzene (13321-73-8) → 5,5'-Bis-benzyloxy-7,7'-bis-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-propyl]-2,6,2',6'-tetramethoxy-4,4'-bis-methoxymethoxy-[1,1']binaphthalenyl (133363-21-0,133443-05-7,133443-06-8,133443-07-9)

Guidance literature:

Multi-step reaction with 22 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

15: MCPBA, Na₂SO₄, 4,4'-methylenebis(2,6-di-t-butyl)phenol / benzene / 1 h / 20 °C

16: aq. NaOH / methanol; tetrahydrofuran / 20 °C

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

18: TBAF

19: DEAD, PPh₃

20: NaOH

22: 1.) t-BuLi, 2.) FeCl₃ / 1.) THF, -78 deg, 2.) -78 deg to 20 deg

With pyridine; 1H-imidazole; sodium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; 4,4'-Methylenebis(2,6-di-tert-butylphenol); tetrabutyl ammonium fluoride; tert.-butyl lithium; boron tribromide; iron(III) chloride; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; sodium sulfate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4039(00)92105-1

Reference yield:

2-bromo-1,5-dimethoxy-3-methylbenzene (13321-73-8) → 5,5'-Bis-benzyloxy-7,7'-bis-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propyl]-2,6,2',6'-tetramethoxy-4,4'-bis-methoxymethoxy-[1,1']binaphthalenyl (133363-21-0,133443-05-7,133443-06-8,133443-07-9)

Guidance literature:

Multi-step reaction with 18 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

15: MCPBA, Na₂SO₄, 4,4'-methylenebis(2,6-di-t-butyl)phenol / benzene / 1 h / 20 °C

16: aq. NaOH / methanol; tetrahydrofuran / 20 °C

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

18: 1.) t-BuLi, 2.) FeCl₃ / 1.) THF, -78 deg, 1 h, 2.) -78 deg to 20 deg, 1.5 h

With pyridine; 1H-imidazole; sodium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; 4,4'-Methylenebis(2,6-di-tert-butylphenol); tert.-butyl lithium; boron tribromide; iron(III) chloride; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; sodium sulfate; 3-chloro-benzenecarboperoxoic 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; benzene;

DOI:10.1016/S0040-4039(00)92105-1

upstream raw materials:

[(R)-2-(4-Benzyloxy-8-bromo-3,7-dimethoxy-5-methoxymethoxy-naphthalen-2-yl)-1-methyl-ethoxy]-tert-butyl-diphenyl-silane

2-bromo-1,5-dimethoxy-3-methylbenzene

2,4-dimethoxy-6-methylbenzoic acid

2,4-dimethoxy-6-methylbenzoyl chloride

Downstream raw materials:

calphostin A

Calphostin D

isophleichrome

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