(E)-3-[(2S,4S,5R)-4-Methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-acrylic acid methyl ester

Base Information

• Chemical Name: (E)-3-[(2S,4S,5R)-4-Methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-acrylic acid methyl ester
• CAS No.: 113323-08-3
• Molecular Formula: C₂₁H₂₃NO₅S
• Molecular Weight: 401.483
• Mol file: 113323-08-3.mol

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

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

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]-acrylic acid methyl ester

There total 1 articles about (E)-3-[(2S,4S,5R)-4-Methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-acrylic acid methyl 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: 85.0%

monofumaraldehyde dimethylacetal monomethylester (32815-00-2) + 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]-acrylic acid methyl ester (113323-08-3)

Guidance literature:

With pyridinium p-toluenesulfonate; In benzene; for 18h; Heating;

DOI:10.1021/jo00243a002

Reference yield: 61.0%

triphenylphosphonio-1-methylethanide (16666-80-1) + (E)-3-[(2S,4S,5R)-4-Methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-acrylic acid methyl ester (113323-08-3) → (1R,3R)-2,2-Dimethyl-3-[(2S,4S,5R)-4-methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-cyclopropanecarboxylic acid methyl ester (125408-43-7)

Guidance literature:

In hexane; benzene; for 0.5h; Ambient temperature;

DOI:10.1016/S0040-4039(01)80496-2

Reference yield:

(E)-3-[(2S,4S,5R)-4-Methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-acrylic acid methyl ester (113323-08-3) → (1R,3R)-hemicaronic aldehyde (26770-99-0,27335-33-7,27335-34-8,41301-44-4,51424-62-5,55701-02-5,62138-41-4,67968-42-7,84710-48-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 61 percent / benzene; hexane / 0.5 h / Ambient temperature

2: 1.) BF_3.Et₂O, HSCH₂CH₂SH, 2.) MeI, CaCO₃ / 2.) H₂O

With boron trifluoride diethyl etherate; ethane-1,2-dithiol; calcium carbonate; methyl iodide; In hexane; benzene;

DOI:10.1016/S0040-4039(01)80496-2

upstream raw materials:

monofumaraldehyde dimethylacetal monomethylester

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

Downstream raw materials:

(1R,3R)-2,2-Dimethyl-3-[(2S,4S,5R)-4-methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-cyclopropanecarboxylic acid methyl ester

(1R,3R)-hemicaronic aldehyde