[4-(5-benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-but-2-enyloxy]-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: [4-(5-benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-but-2-enyloxy]-tert-butyl-dimethyl-silane
• CAS No.: 693784-45-1
• Molecular Formula: C₃₀H₃₉BrO₅Si
• Molecular Weight: 587.626

Synonyms:[4-(5-benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-but-2-enyloxy]-tert-butyl-dimethyl-silane

Chemical Property of [4-(5-benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-but-2-enyloxy]-tert-butyl-dimethyl-silane

Chemical Property:

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Technology Process of [4-(5-benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-but-2-enyloxy]-tert-butyl-dimethyl-silane

There total 9 articles about [4-(5-benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-but-2-enyloxy]-tert-butyl-dimethyl-silane 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: 96.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (E)-4-(5-Benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-but-2-en-1-ol (693784-38-2) → [4-(5-benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-but-2-enyloxy]-tert-butyl-dimethyl-silane (693784-45-1)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/j.tetlet.2003.11.120

Reference yield:

5-(benzyloxy)-2,3-dimethoxybenzaldehyde (93092-16-1) → [4-(5-benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-but-2-enyloxy]-tert-butyl-dimethyl-silane (693784-45-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: NaH / tetrahydrofuran / 20 °C

1.2: 77 percent / TFA / H₂O / 20 °C

2.1: 92 percent / KOAc / Heating

3.1: K₂CO₃ / ethanol / 20 °C

4.1: LiAlH₄ / tetrahydrofuran / 20 °C

5.1: Pyr*HBr₃ / tetrahydrofuran / 0 °C

6.1: 93 percent / SO₃*Py; TEA; DMSO / CH₂Cl₂ / 20 °C

7.1: 94 percent / K₂CO₃ / dimethylformamide / 20 °C

8.1: 92 percent / NaH / dimethylsulfoxide; tetrahydrofuran / 0 °C

9.1: ZnBr₂ / benzene / Heating

10.1: NaH / tetrahydrofuran / -78 °C

11.1: 93 percent / DIBAL / tetrahydrofuran / -78 °C

12.1: 96 percent / imidazol / dimethylformamide / 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; pyridine-SO₃ complex; TEA; potassium acetate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; pyridinium hydrobromide perbromide; zinc dibromide; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene; 1.1: Horner-Wadsworth-Emmons / 10.1: Horner-Wadsworth-Emmons olefination;

DOI:10.1016/j.tetlet.2003.11.120

Reference yield:

5-benzyloxy-3-bromo-4,7,8-trimethoxynaphthalene-2-carbaldehyde (693784-42-8) → [4-(5-benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-but-2-enyloxy]-tert-butyl-dimethyl-silane (693784-45-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / NaH / dimethylsulfoxide; tetrahydrofuran / 0 °C

2: ZnBr₂ / benzene / Heating

3: NaH / tetrahydrofuran / -78 °C

4: 93 percent / DIBAL / tetrahydrofuran / -78 °C

5: 96 percent / imidazol / dimethylformamide / 20 °C

With 1H-imidazole; sodium hydride; diisobutylaluminium hydride; zinc dibromide; In tetrahydrofuran; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene; 3: Horner-Wadsworth-Emmons olefination;

DOI:10.1016/j.tetlet.2003.11.120

upstream raw materials:

tert-butyldimethylsilyl chloride

(E)-4-(5-Benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-but-2-en-1-ol

5-(benzyloxy)-2,3-dimethoxybenzaldehyde

5-benzyloxy-3-bromo-4,7,8-trimethoxynaphthalene-2-carbaldehyde

Downstream raw materials:

Acetic acid (E)-4-[5-benzyloxy-3-(1-hydroxy-pentyl)-4,7,8-trimethoxy-naphthalen-2-yl]-but-2-enyl ester

1-[8-Benzyloxy-3-((E)-4-hydroxy-but-2-enyl)-1,5,6-trimethoxy-naphthalen-2-yl]-pentan-1-ol

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