ethyl (2R,3S)-2,3-dihydroxy-3-[4-(methylsulfonyl)phenyl]propanoate

Base Information

• Chemical Name: ethyl (2R,3S)-2,3-dihydroxy-3-[4-(methylsulfonyl)phenyl]propanoate
• CAS No.: 1373543-38-4
• Molecular Formula: C₁₂H₁₆O₆S
• Molecular Weight: 288.321
• Mol file: 1373543-38-4.mol

Synonyms:ethyl (2R,3S)-2,3-dihydroxy-3-[4-(methylsulfonyl)phenyl]propanoate

Chemical Property of ethyl (2R,3S)-2,3-dihydroxy-3-[4-(methylsulfonyl)phenyl]propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (2R,3S)-2,3-dihydroxy-3-[4-(methylsulfonyl)phenyl]propanoate

There total 3 articles about ethyl (2R,3S)-2,3-dihydroxy-3-[4-(methylsulfonyl)phenyl]propanoate 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%

ethyl (2E)-3-[4-(methylsulfonyl)phenyl]acrylate (137473-27-9) → ethyl (2R,3S)-2,3-dihydroxy-3-[4-(methylsulfonyl)phenyl]propanoate (1373543-38-4)

Guidance literature:

With methanesulfonamide; AD-mix-α; water; In tert-butyl alcohol; at 25 ℃; for 20h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1055/s-0031-1289706

Reference yield:

para-methanesulfonylbenzaldehyde (5398-77-6) → ethyl (2R,3S)-2,3-dihydroxy-3-[4-(methylsulfonyl)phenyl]propanoate (1373543-38-4)

Guidance literature:

Multi-step reaction with 3 steps

1: piperidine; pyridine / 2 h / Inert atmosphere; Reflux

2: thionyl chloride / 20 °C / Inert atmosphere; Reflux

3: AD-mix-α; methanesulfonamide; water / tert-butyl alcohol / 20 h / 25 °C / Inert atmosphere

With piperidine; pyridine; thionyl chloride; methanesulfonamide; AD-mix-α; water; In tert-butyl alcohol; 1: Knoevenagel condensation / 3: Sharpless dihydroxylation;

DOI:10.1055/s-0031-1289706

Reference yield:

3-(4-methanesulfonyl-phenyl)-acrylic acid (5345-30-2,88899-85-8) → ethyl (2R,3S)-2,3-dihydroxy-3-[4-(methylsulfonyl)phenyl]propanoate (1373543-38-4)

Guidance literature:

Multi-step reaction with 2 steps

1: thionyl chloride / 20 °C / Inert atmosphere; Reflux

2: AD-mix-α; methanesulfonamide; water / tert-butyl alcohol / 20 h / 25 °C / Inert atmosphere

With thionyl chloride; methanesulfonamide; AD-mix-α; water; In tert-butyl alcohol; 2: Sharpless dihydroxylation;

DOI:10.1055/s-0031-1289706

upstream raw materials:

para-methanesulfonylbenzaldehyde

3-(4-methanesulfonyl-phenyl)-acrylic acid

ethyl (2E)-3-[4-(methylsulfonyl)phenyl]acrylate

Downstream raw materials:

ethyl (2R,3S)-3-hydroxy-3-[4-(methylsulfonyl)phenyl]-2-{[(4-nitrophenyl)sulfonyl]oxy}propanoate