2,4-di-O-benzoyl ascarylose

Base Information

• Chemical Name: 2,4-di-O-benzoyl ascarylose
• CAS No.: 104768-14-1
• Molecular Formula: C₂₀H₂₀O₆
• Molecular Weight: 356.375
• Mol file: 104768-14-1.mol

Synonyms:2,4-di-O-benzoyl ascarylose

Chemical Property of 2,4-di-O-benzoyl ascarylose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,4-di-O-benzoyl ascarylose

There total 4 articles about 2,4-di-O-benzoyl ascarylose 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:

2,4-di-O-benzoyl-3,6-dideoxy-L-arabino-hexono-1,5-lactone (69992-14-9) → (2R,3R,5R,6S)-2-hydroxy-6-methyltetrahydro-2H-pyran-3,5-diyl dibenzoate (104768-13-0) + 2,4-di-O-benzoyl ascarylose (104768-14-1)

Guidance literature:

2,4-di-O-benzoyl-3,6-dideoxy-L-arabino-hexono-1,5-lactone; With bis-(1,2-dimethylpropyl)borane; In tetrahydrofuran; at 20 ℃; for 20h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 0 ℃; pH=7 - 8;

Reference yield:

2,4-di-O-benzoyl-1-O-methyl ascarylose (69992-16-1) → (2R,3R,5R,6S)-2-hydroxy-6-methyltetrahydro-2H-pyran-3,5-diyl dibenzoate (104768-13-0) + 2,4-di-O-benzoyl ascarylose (104768-14-1)

Guidance literature:

With boron tribromide; In dichloromethane; at -70 - -65 ℃; for 1h; Overall yield = 61 percent; Overall yield = 235 mg;

DOI:10.1021/acs.orglett.0c02038

Reference yield:

L-rhamnose (6014-42-2) → (2R,3R,5R,6S)-2-hydroxy-6-methyltetrahydro-2H-pyran-3,5-diyl dibenzoate (104768-13-0) + 2,4-di-O-benzoyl ascarylose (104768-14-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sulfuric acid / 120 h / Reflux

2.1: dibutyltin chloride; N-ethyl-N,N-diisopropylamine; p-toluenesulfonyl chloride / acetonitrile / 2 h / 20 °C

2.2: 1 h / Reflux

2.3: 24 h / 0 - 20 °C

3.1: boron tribromide / dichloromethane / 1 h / -70 - -65 °C

With sulfuric acid; dibutyltin chloride; boron tribromide; N-ethyl-N,N-diisopropylamine; p-toluenesulfonyl chloride; In dichloromethane; acetonitrile;

DOI:10.1021/acs.orglett.0c02038

upstream raw materials:

2,4-di-O-benzoyl-3,6-dideoxy-L-arabino-hexono-1,5-lactone

L-rhamnose

methyl 6-deoxy-α-L-mannopyranoside

2,4-di-O-benzoyl-1-O-methyl ascarylose

Refernces

• 1、 Martin, Rene,Schaefer, Tina,Theumer, Gabriele,Entchev, Eugeni V.,Kurzchalia, Teymuras V.,Knoelker, Hans-Joachim. "Improved synthesis of an ascaroside pheromone controlling dauer larva development in caenorhabditis elegans". scheme or table. p. 3488 - 3492. Retrieved 2010/03/02.