(1S,2S,3S,4S,6R)-3-(4-bromobenzoyl)-7,9-dioxatricyclo[4.2.1.0^2,4]nonan-5-one

Base Information

• Chemical Name: (1S,2S,3S,4S,6R)-3-(4-bromobenzoyl)-7,9-dioxatricyclo[4.2.1.0^2,4]nonan-5-one
• CAS No.: 956480-87-8
• Molecular Formula: C₁₄H₁₁BrO₄
• Molecular Weight: 323.143
• Mol file: 956480-87-8.mol

Synonyms:(1S,2S,3S,4S,6R)-3-(4-bromobenzoyl)-7,9-dioxatricyclo[4.2.1.0^2,4]nonan-5-one

Chemical Property of (1S,2S,3S,4S,6R)-3-(4-bromobenzoyl)-7,9-dioxatricyclo[4.2.1.0^2,4]nonan-5-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3S,4S,6R)-3-(4-bromobenzoyl)-7,9-dioxatricyclo[4.2.1.0^2,4]nonan-5-one

There total 2 articles about (1S,2S,3S,4S,6R)-3-(4-bromobenzoyl)-7,9-dioxatricyclo[4.2.1.0^2,4]nonan-5-one 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: 84.0%

levoglucosenone (37112-31-5) + (4-bromophenacyl)dimethylsulfanium bromide (6047-83-2) → (1S,2S,3S,4S,6R)-3-(4-bromobenzoyl)-7,9-dioxatricyclo[4.2.1.02,4]nonan-5-one (956480-87-8)

Guidance literature:

With triethylamine; In ethanol; at 35 - 40 ℃; for 3h;

DOI:10.1016/j.tetasy.2007.08.013

Reference yield:

para-bromophenacyl bromide (99-73-0,132309-76-3) → (1S,2S,3S,4S,6R)-3-(4-bromobenzoyl)-7,9-dioxatricyclo[4.2.1.02,4]nonan-5-one (956480-87-8)

Guidance literature:

Multi-step reaction with 2 steps

1: acetone / 24 h / 0 °C

2: 84 percent / Et₃N / ethanol / 3 h / 35 - 40 °C

With triethylamine; In ethanol; acetone;

DOI:10.1016/j.tetasy.2007.08.013

Reference yield: 82.0%

(1S,2S,3S,4S,6R)-3-(4-bromobenzoyl)-7,9-dioxatricyclo[4.2.1.02,4]nonan-5-one (956480-87-8) → (1S,2S,3S)-2-(4-bromobenzoyl)-3-((S)-2-formyloxy-1-hydroxyethyl)cyclopropanecarboxylic acid (1030901-03-1)

Guidance literature:

With dihydrogen peroxide; acetic acid; at 30 - 40 ℃;

DOI:10.1016/j.tetasy.2008.02.016

upstream raw materials:

levoglucosenone

(4-bromophenacyl)dimethylsulfanium bromide

para-bromophenacyl bromide

Downstream raw materials:

(1S,2S,3S)-2-(4-bromobenzoyl)-3-((S)-2-formyloxy-1-hydroxyethyl)cyclopropanecarboxylic acid