(2S,3R)-3-Hydroxy-3-(4-methoxy-phenyl)-2-(toluene-4-sulfonyloxy)-propionic acid ethyl ester

Base Information

• Chemical Name: (2S,3R)-3-Hydroxy-3-(4-methoxy-phenyl)-2-(toluene-4-sulfonyloxy)-propionic acid ethyl ester
• CAS No.: 780795-86-0
• Molecular Formula: C₁₉H₂₂O₇S
• Molecular Weight: 394.445
• Mol file: 780795-86-0.mol

Synonyms:(2S,3R)-3-Hydroxy-3-(4-methoxy-phenyl)-2-(toluene-4-sulfonyloxy)-propionic acid ethyl ester

Chemical Property of (2S,3R)-3-Hydroxy-3-(4-methoxy-phenyl)-2-(toluene-4-sulfonyloxy)-propionic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-3-Hydroxy-3-(4-methoxy-phenyl)-2-(toluene-4-sulfonyloxy)-propionic acid ethyl ester

There total 3 articles about (2S,3R)-3-Hydroxy-3-(4-methoxy-phenyl)-2-(toluene-4-sulfonyloxy)-propionic acid ethyl ester 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%

p-toluenesulfonyl chloride (98-59-9) + ethyl (2S,3R)-2,3-dihydroxy-3-(4-methoxyphenyl)propanoate (159848-77-8) → (2S,3R)-3-Hydroxy-3-(4-methoxy-phenyl)-2-(toluene-4-sulfonyloxy)-propionic acid ethyl ester (780795-86-0)

Guidance literature:

With triethylamine; In dichloromethane; at 5 ℃; for 72h;

DOI:10.1016/j.tetlet.2004.07.157

Reference yield:

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate (24393-56-4) → (2S,3R)-3-Hydroxy-3-(4-methoxy-phenyl)-2-(toluene-4-sulfonyloxy)-propionic acid ethyl ester (780795-86-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / (DHQD)2PHAL; OsO₄ / 2-methyl-propan-2-ol; H₂O / 16 h / 0 °C

2: 95 percent / Et₃N / CH₂Cl₂ / 72 h / 5 °C

With osmium(VIII) oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; In dichloromethane; water; tert-butyl alcohol;

DOI:10.1016/j.tetlet.2004.07.157

Reference yield:

4-methoxy-benzaldehyde (123-11-5) → (2S,3R)-3-Hydroxy-3-(4-methoxy-phenyl)-2-(toluene-4-sulfonyloxy)-propionic acid ethyl ester (780795-86-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 82 percent / basic alumina / microwave irradiation

2: 94 percent / (DHQD)2PHAL; OsO₄ / 2-methyl-propan-2-ol; H₂O / 16 h / 0 °C

3: 95 percent / Et₃N / CH₂Cl₂ / 72 h / 5 °C

With aluminum oxide; osmium(VIII) oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; In dichloromethane; water; tert-butyl alcohol; 1: Wittig olefination;

DOI:10.1016/j.tetlet.2004.07.157

upstream raw materials:

p-toluenesulfonyl chloride

ethyl (2S,3R)-2,3-dihydroxy-3-(4-methoxyphenyl)propanoate

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

4-methoxy-benzaldehyde

Downstream raw materials:

(+)-(4S,5S)-5-(hydroxymethyl)-4-(4-methoxyphenyl)-1,3-oxazolidin-2-one

(2S,3S)-3-Azido-2-hydroxy-3-(4-methoxy-phenyl)-propionic acid ethyl ester

(2S,3R)-trans-(4-methoxyphenyl)glycidic acid ethyl ester