2-(5-benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-oxirane

Base Information

• Chemical Name: 2-(5-benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-oxirane
• CAS No.: 693784-43-9
• Molecular Formula: C₂₂H₂₁BrO₅
• Molecular Weight: 445.31
• Mol file: 693784-43-9.mol

Synonyms:2-(5-benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-oxirane

Chemical Property of 2-(5-benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-oxirane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(5-benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-oxirane

There total 9 articles about 2-(5-benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-oxirane 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: 92.0%

trimethylsulfonium iodide (1030268-21-3) + 5-benzyloxy-3-bromo-4,7,8-trimethoxynaphthalene-2-carbaldehyde (693784-42-8) → 2-(5-benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-oxirane (693784-43-9)

Guidance literature:

With sodium hydride; In tetrahydrofuran; dimethyl sulfoxide; at 0 ℃;

DOI:10.1016/j.tetlet.2003.11.120

Reference yield:

trimethylsulphonium iodide (2181-42-2) + 5-benzyloxy-3-bromo-4,7,8-trimethoxynaphthalene-2-carbaldehyde (693784-42-8) → 2-(5-benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-oxirane (693784-43-9)

Guidance literature:

trimethylsulphonium iodide; With sodium hydride; dimethyl sulfoxide; In tetrahydrofuran; at 0 - 5 ℃; for 0.666667h;

5-benzyloxy-3-bromo-4,7,8-trimethoxynaphthalene-2-carbaldehyde; In tetrahydrofuran; dimethyl sulfoxide; at 0 ℃; for 0.916667h;

DOI:10.1246/bcsj.77.1925

Reference yield:

5-benzyloxy-3-bromo-4-hydroxy-7,8-dimethoxy-naphthalene-2-carbaldehyde (693784-37-1) → 2-(5-benzyloxy-3-bromo-4,7,8-trimethoxy-naphthalen-2-yl)-oxirane (693784-43-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 2.32 g / K₂CO₃ / dimethylformamide / 1 h / 20 °C

2.1: NaH; DMSO / tetrahydrofuran / 0.67 h / 0 - 5 °C

2.2: tetrahydrofuran; dimethylsulfoxide / 0.92 h / 0 °C

With sodium hydride; potassium carbonate; dimethyl sulfoxide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.77.1925

upstream raw materials:

trimethylsulfonium iodide

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

trimethylsulphonium iodide

8-benzyloxy-3-hydroxymethyl-5,6-dimethoxy-1-naphthol

Downstream raw materials:

(2E)-4-(5-benzyloxy-3-bromo-4,7,8-trimethoxy-2-naphthyl)but-2-en-1-ol

ethyl (2E)-4-(5-benzyloxy-3-bromo-4,7,8-trimethoxy-2-naphthyl)but-2-enoate

8-benzyloxy-2-bromo-3-[(2E)-4-(t-butyldimethylsiloxy)-2-butenyl]-1,5,6-trimethoxynaphthalene

(2E)-4-(5-benzyloxy-3-(1-hydroxypentyl)-4,7,8-trimethoxy-2-naphthyl)but-2-en-1-ol