5-benzyloxy-8-bromo-1,4-dimethoxy-7-methoxymethoxy-2,6-dimethyl-3-[2-(trimethylsilyl)ethoxycarbonyl]naphthalene

Base Information

Chemical Name:5-benzyloxy-8-bromo-1,4-dimethoxy-7-methoxymethoxy-2,6-dimethyl-3-[2-(trimethylsilyl)ethoxycarbonyl]naphthalene
CAS No.:148117-07-1
Molecular Formula:C₂₉H₃₇BrO₇Si
Molecular Weight:605.598
Hs Code.:

Synonyms:5-benzyloxy-8-bromo-1,4-dimethoxy-7-methoxymethoxy-2,6-dimethyl-3-[2-(trimethylsilyl)ethoxycarbonyl]naphthalene

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Chemical Property of 5-benzyloxy-8-bromo-1,4-dimethoxy-7-methoxymethoxy-2,6-dimethyl-3-[2-(trimethylsilyl)ethoxycarbonyl]naphthalene

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Technology Process of 5-benzyloxy-8-bromo-1,4-dimethoxy-7-methoxymethoxy-2,6-dimethyl-3-[2-(trimethylsilyl)ethoxycarbonyl]naphthalene

There total 9 articles about 5-benzyloxy-8-bromo-1,4-dimethoxy-7-methoxymethoxy-2,6-dimethyl-3-[2-(trimethylsilyl)ethoxycarbonyl]naphthalene 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: 93.0%

: 107-30-2
chloromethyl methyl ether

: 148117-06-0
5-benzyloxy-1,4-dimethoxy-7-methoxymethoxy-2,6-dimethyl-3-[2-(trimethylsilyl)ethoxycarbonyl]naphthalene

: 148117-07-1
5-benzyloxy-8-bromo-1,4-dimethoxy-7-methoxymethoxy-2,6-dimethyl-3-[2-(trimethylsilyl)ethoxycarbonyl]naphthalene

Guidance literature:: 5-benzyloxy-1,4-dimethoxy-7-methoxymethoxy-2,6-dimethyl-3-[2-(trimethylsilyl)ethoxycarbonyl]naphthalene; With N-Bromosuccinimide; In chloroform; for 8h; Heating;

chloromethyl methyl ether; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 23 ℃; for 1h;
DOI:10.1139/cjc-79-11-1711

Reference yield:

: 85954-40-1
3-Bromo-5,7-dihydroxy-2,6-dimethyl-[1,4]naphthoquinone

: 148117-07-1
5-benzyloxy-8-bromo-1,4-dimethoxy-7-methoxymethoxy-2,6-dimethyl-3-[2-(trimethylsilyl)ethoxycarbonyl]naphthalene

Guidance literature:: Multi-step reaction with 6 steps

1.1: P₂O₅ / CHCl₃

2.1: 90 percent / Ag₂O / CHCl₃ / 24 h / 23 °C

3.1: CeCl₃*7H₂O; NaBH₄ / dioxane; H₂O / 0 °C

3.2: 89 percent / 50 percent NaOH / dioxane; H₂O / 1 h / 23 °C

4.1: 90 percent / n-BuLi / tetrahydrofuran / 3 h / -78 - 23 °C

5.1: 85 percent / PPh₃; diethyl azodicarboxylate / tetrahydrofuran / 4 h / 23 °C

6.1: N-bromosuccinimide / CHCl₃ / 8 h / Heating

6.2: 93 percent / i-Pr₂NEt / CH₂Cl₂ / 1 h / 23 °C

With sodium tetrahydroborate; N-Bromosuccinimide; n-butyllithium; cerium(III) chloride; phosphorus pentoxide; triphenylphosphine; silver(l) oxide; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; chloroform; water; 5.1: Mitsunobu reaction;
DOI:10.1139/cjc-79-11-1711

Reference yield:

: 85954-41-2
3-Bromo-5-hydroxy-7-methoxymethoxy-2,6-dimethyl-[1,4]naphthoquinone

: 148117-07-1
5-benzyloxy-8-bromo-1,4-dimethoxy-7-methoxymethoxy-2,6-dimethyl-3-[2-(trimethylsilyl)ethoxycarbonyl]naphthalene

Guidance literature:: Multi-step reaction with 5 steps

1.1: 90 percent / Ag₂O / CHCl₃ / 24 h / 23 °C

2.1: CeCl₃*7H₂O; NaBH₄ / dioxane; H₂O / 0 °C

2.2: 89 percent / 50 percent NaOH / dioxane; H₂O / 1 h / 23 °C

3.1: 90 percent / n-BuLi / tetrahydrofuran / 3 h / -78 - 23 °C

4.1: 85 percent / PPh₃; diethyl azodicarboxylate / tetrahydrofuran / 4 h / 23 °C

5.1: N-bromosuccinimide / CHCl₃ / 8 h / Heating

5.2: 93 percent / i-Pr₂NEt / CH₂Cl₂ / 1 h / 23 °C

With sodium tetrahydroborate; N-Bromosuccinimide; n-butyllithium; cerium(III) chloride; triphenylphosphine; silver(l) oxide; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; chloroform; water; 4.1: Mitsunobu reaction;
DOI:10.1139/cjc-79-11-1711