5,6-O-isopropylidene-3-O-trans-cinnamyl-2-O-acetyl-L-ascorbic acid

Base Information

• Chemical Name: 5,6-O-isopropylidene-3-O-trans-cinnamyl-2-O-acetyl-L-ascorbic acid
• CAS No.: 790702-24-8
• Molecular Formula: C₂₀H₂₂O₇
• Molecular Weight: 374.39
• Mol file: 790702-24-8.mol

Synonyms:5,6-O-isopropylidene-3-O-trans-cinnamyl-2-O-acetyl-L-ascorbic acid

Chemical Property of 5,6-O-isopropylidene-3-O-trans-cinnamyl-2-O-acetyl-L-ascorbic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5,6-O-isopropylidene-3-O-trans-cinnamyl-2-O-acetyl-L-ascorbic acid

There total 2 articles about 5,6-O-isopropylidene-3-O-trans-cinnamyl-2-O-acetyl-L-ascorbic acid 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: 76.0%

Cinnamyl bromide (4392-24-9) + [(2R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-5-oxo-2H-furan-4-yl] acetate (116565-60-7) → 5,6-O-isopropylidene-3-O-trans-cinnamyl-2-O-acetyl-L-ascorbic acid (790702-24-8)

Guidance literature:

potassium carbonate; In tetrahydrofuran; dimethyl sulfoxide; for 20h;

DOI:10.1021/jo049319i

Reference yield:

5,6-O-isopropylidene-L-ascorbic acid (15042-01-0) → 5,6-O-isopropylidene-3-O-trans-cinnamyl-2-O-acetyl-L-ascorbic acid (790702-24-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / pyridine / CH₂Cl₂ / 2 h / 20 °C

2: 76 percent / K₂CO₃ / dimethylsulfoxide; tetrahydrofuran / 20 h

With pyridine; potassium carbonate; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/jo049319i

Reference yield:

5,6-O-isopropylidene-3-O-trans-cinnamyl-2-O-acetyl-L-ascorbic acid (790702-24-8) → Acetic acid (3R,5R)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,4-dioxo-3-(1-phenyl-allyl)-tetrahydro-furan-3-yl ester + 5,6-O-isopropylidene-3-keto-2-O-acetyl-2-(1-phenyl-1-prop-2-enyl)-L-galactono-γ-lactone

Guidance literature:

In toluene; for 6h; Heating;

DOI:10.1021/jo0508550

upstream raw materials:

Cinnamyl bromide

[(2R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-5-oxo-2H-furan-4-yl] acetate

5,6-O-isopropylidene-L-ascorbic acid