(S)-2-[(2R,4R)-4-Phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-cyclohexanone

Base Information

• Chemical Name: (S)-2-[(2R,4R)-4-Phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-cyclohexanone
• CAS No.: 118832-18-1
• Molecular Formula: C₂₂H₂₅NO₄S
• Molecular Weight: 399.511
• Mol file: 118832-18-1.mol

Synonyms:(S)-2-[(2R,4R)-4-Phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-cyclohexanone

Chemical Property of (S)-2-[(2R,4R)-4-Phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-cyclohexanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-[(2R,4R)-4-Phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-cyclohexanone

There total 4 articles about (S)-2-[(2R,4R)-4-Phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-cyclohexanone 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: 71.0%

(R)-N-(2-hydroxy-1-phenylethyl)-4-methyl-S-methylenebenzenesulfinamide (118917-59-2) + 2-(hydroxymethylene)cyclohexanone (823-45-0) → (S)-2-[(2R,4R)-4-Phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-cyclohexanone (118832-18-1) + (R)-2-[(2R,4R)-4-Phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-cyclohexanone (128504-54-1)

Guidance literature:

With methanesulfonic acid; 4 A molecular sieve; In dichloromethane; at 25 ℃; for 24h; Yields of byproduct given;

DOI:10.1055/s-1991-28410

Reference yield: 71.0%

2-(hydroxymethylene)cyclohexanone (39695-64-2) + (R)-N-(2-hydroxy-1-phenylethyl)-4-methyl-S-methylenebenzenesulfinamide (118917-59-2) → (S)-2-[(2R,4R)-4-Phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-cyclohexanone (118832-18-1)

Guidance literature:

With molecular sieve; methanesulfonic acid; In dichloromethane; at 20 - 25 ℃; for 24h;

Reference yield:

D-2-phenylglycinol (56613-80-0) → (S)-2-[(2R,4R)-4-Phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-cyclohexanone (118832-18-1)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / CH₂Cl₂ / 24 h / 0 °C

2: methanesulfonic acid, molecular sieves 4 Angstroem / CH₂Cl₂ / 24 h / 25 °C

With methanesulfonic acid; 4 A molecular sieve; triethylamine; In dichloromethane;

DOI:10.1055/s-1991-28410

upstream raw materials:

2-(hydroxymethylene)cyclohexanone

(R)-N-(2-hydroxy-1-phenylethyl)-4-methyl-S-methylenebenzenesulfinamide

2-(hydroxymethylene)cyclohexanone

D-2-phenylglycinol

Downstream raw materials:

(1R,2R)-2-[(2R,4R)-4-Phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-1-vinyl-cyclohexanol

(1S,2R)-1-Phenyl-2-[(2R,4R)-4-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-cyclohexanol

(2S,6S)-2-((1R,2S)-2-Benzyloxy-1-hydroxy-propyl)-6-[(2R,4R)-4-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-cyclohexanone

(1S,2R)-1-Methyl-2-[(2R,4R)-4-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-cyclohexanol