(E)-3-[(2S,4S,5R)-4-Methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-propenal

Base Information

• Chemical Name: (E)-3-[(2S,4S,5R)-4-Methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-propenal
• CAS No.: 119588-68-0
• Molecular Formula: C₂₀H₂₁NO₄S
• Molecular Weight: 371.457
• Mol file: 119588-68-0.mol

Synonyms:(E)-3-[(2S,4S,5R)-4-Methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-propenal

Chemical Property of (E)-3-[(2S,4S,5R)-4-Methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-propenal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-[(2S,4S,5R)-4-Methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-propenal

There total 2 articles about (E)-3-[(2S,4S,5R)-4-Methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-propenal 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:

(2S,4S,5R)-2-((E)-3,3-Dimethoxy-propenyl)-4-methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidine → (E)-3-[(2S,4S,5R)-4-Methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-propenal (119588-68-0)

Guidance literature:

With amberlyst-15; In water; acetone; for 3h; Yield given; Ambient temperature;

DOI:10.1016/S0040-4020(01)86061-0

Reference yield:

N-((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)-4-methylbenzene sulfonamide (108591-33-9) → (E)-3-[(2S,4S,5R)-4-Methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-propenal (119588-68-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / pyridinium tosylate / benzene / 0.5 h / Heating

2: Amberlyst-15 / acetone; H₂O / 3 h / Ambient temperature

With amberlyst-15; pyridinium p-toluenesulfonate; In water; acetone; benzene;

DOI:10.1016/S0040-4020(01)86061-0

Reference yield: 90.0%

(E)-3-[(2S,4S,5R)-4-Methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-propenal (119588-68-0) → (2R,3S)-3-[(2S,4S,5R)-4-Methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-oxirane-2-carbaldehyde

Guidance literature:

With potassium hypochlorite; In tetrahydrofuran; water; 1 h 0 degC then 2 h r.t.;

DOI:10.1016/S0040-4020(01)86061-0

upstream raw materials:

N-((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)-4-methylbenzene sulfonamide

Downstream raw materials:

(2S,3S)-2-Amino-3-hydroxy-3-[(2S,4S,5R)-4-methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-propionic acid; hydrochloride

(2R,3S)-2-Amino-3-hydroxy-3-[(2S,4S,5R)-4-methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-propionic acid

(2S,4S,5R,4'S,5'S)-4-Methyl-2'-oxo-5-phenyl-3-(toluene-4-sulfonyl)-[2,5']bioxazolidinyl-4'-carboxylic acid methyl ester

(2S,4S,5R,4'R,5'S)-4-Methyl-2'-oxo-5-phenyl-3-(toluene-4-sulfonyl)-[2,5']bioxazolidinyl-4'-carboxylic acid methyl ester