(4R,5S)-5-Benzyloxymethyl-4-(2-methoxy-benzoyl)-4-methyl-[1,3]dioxolan-2-one

Base Information

• Chemical Name: (4R,5S)-5-Benzyloxymethyl-4-(2-methoxy-benzoyl)-4-methyl-[1,3]dioxolan-2-one
• CAS No.: 503473-24-3
• Molecular Formula: C₂₀H₂₀O₆
• Molecular Weight: 356.375
• Mol file: 503473-24-3.mol

Synonyms:(4R,5S)-5-Benzyloxymethyl-4-(2-methoxy-benzoyl)-4-methyl-[1,3]dioxolan-2-one

Chemical Property of (4R,5S)-5-Benzyloxymethyl-4-(2-methoxy-benzoyl)-4-methyl-[1,3]dioxolan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S)-5-Benzyloxymethyl-4-(2-methoxy-benzoyl)-4-methyl-[1,3]dioxolan-2-one

There total 1 articles about (4R,5S)-5-Benzyloxymethyl-4-(2-methoxy-benzoyl)-4-methyl-[1,3]dioxolan-2-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: 95.0%

4-benzyloxy-2,3-dihydroxy-1-(2-methoxy-phenyl)-2-methyl-butan-1-one + bis(trichloromethyl) carbonate (32315-10-9) → (4R,5S)-5-Benzyloxymethyl-4-(2-methoxy-benzoyl)-4-methyl-[1,3]dioxolan-2-one (503473-24-3) + (4S,5R)-5-Benzyloxymethyl-4-(2-methoxy-benzoyl)-4-methyl-[1,3]dioxolan-2-one

Guidance literature:

With pyridine; In dichloromethane; at -78 - 20 ℃; Title compound not separated from byproducts;

DOI:10.1021/ja028926p

Reference yield:

(4R,5S)-5-Benzyloxymethyl-4-(2-methoxy-benzoyl)-4-methyl-[1,3]dioxolan-2-one (503473-24-3) → (4R,5S)-5-Benzyloxymethyl-4-methyl-2-oxo-[1,3]dioxolane-4-carboxylic acid (2-methoxy-phenyl)-amide

Guidance literature:

With mesitylenesulfonylhydroxylamine; In 1,2-dichloro-ethane; at 60 ℃; for 8h;

DOI:10.1021/ja028926p

Reference yield:

(4R,5S)-5-Benzyloxymethyl-4-(2-methoxy-benzoyl)-4-methyl-[1,3]dioxolan-2-one (503473-24-3) → (4R,5S)-5-Benzyloxymethyl-2,2,4-trimethyl-[1,3]dioxolane-4-carbaldehyde

Guidance literature:

Multi-step reaction with 4 steps

1: O-mesitylenesulfonylhydroxilamine / 1,2-dichloro-ethane / 8 h / 60 °C

2: NaOMe / methanol / 0.33 h

3: TsOH*H₂O

4: DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

With sodium methylate; mesitylenesulfonylhydroxylamine; diisobutylaluminium hydride; toluene-4-sulfonic acid; In methanol; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1021/ja028926p

upstream raw materials:

bis(trichloromethyl) carbonate

Downstream raw materials:

(2S,3S)-4-(benzyloxy)-2-methylbutane-1,2,3-triol

((4S,5S)-5-Benzyloxymethyl-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-methanol

(4R,5S)-5-Benzyloxymethyl-2,2,4-trimethyl-[1,3]dioxolane-4-carboxylic acid (2-methoxy-phenyl)-amide