3-Oxazolidinecarboxylic acid, 4-[(R)-hydroxy(2-hydroxy-4-methoxyphenyl)methyl]-2,2-dimethyl-, 1,1-dimethylethyl ester, (4R)-

Base Information

• Chemical Name: 3-Oxazolidinecarboxylic acid, 4-[(R)-hydroxy(2-hydroxy-4-methoxyphenyl)methyl]-2,2-dimethyl-, 1,1-dimethylethyl ester, (4R)-
• CAS No.: 925703-63-5
• Molecular Formula: C18H27NO6
• Molecular Weight: 353.415
• Mol file: 925703-63-5.mol

Synonyms:

Chemical Property of 3-Oxazolidinecarboxylic acid, 4-[(R)-hydroxy(2-hydroxy-4-methoxyphenyl)methyl]-2,2-dimethyl-, 1,1-dimethylethyl ester, (4R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-Oxazolidinecarboxylic acid, 4-[(R)-hydroxy(2-hydroxy-4-methoxyphenyl)methyl]-2,2-dimethyl-, 1,1-dimethylethyl ester, (4R)-

There total 1 articles about 3-Oxazolidinecarboxylic acid, 4-[(R)-hydroxy(2-hydroxy-4-methoxyphenyl)methyl]-2,2-dimethyl-, 1,1-dimethylethyl ester, (4R)- 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: 100.0%

O-methylresorcine (150-19-6) + (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine (95715-87-0) → tert-butyl (R)-4-((R)-hydroxy(2-hydroxy-4-methoxyphenyl)methyl)-2,2-dimethyloxazolidine-3-carboxylate (925703-63-5)

Guidance literature:

O-methylresorcine; With methylmagnesium chloride; In tetrahydrofuran; at 20 ℃; for 0.166667h;

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine; In dichloromethane; at 0 - 20 ℃; for 15h;

DOI:10.1021/ol0627202

Reference yield:

tert-butyl (R)-4-((R)-hydroxy(2-hydroxy-4-methoxyphenyl)methyl)-2,2-dimethyloxazolidine-3-carboxylate (925703-63-5) + allyl bromide (106-95-6) → 4-[(2-allyloxy-4-methoxy-phenyl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:

With potassium carbonate; sodium iodide; In acetone; at 20 ℃; for 16h;

DOI:10.1021/ol0627202

Reference yield:

tert-butyl (R)-4-((R)-hydroxy(2-hydroxy-4-methoxyphenyl)methyl)-2,2-dimethyloxazolidine-3-carboxylate (925703-63-5) → (4S,5S)-4-(2-allyloxy-4-methoxyphenyl)-5-(hydroxymethyl)imidazolidin-2-one

Guidance literature:

Multi-step reaction with 4 steps

1: K₂CO₃; NaI / acetone / 16 h / 20 °C

2: p-toluenesulfonic acid / methanol / 2 h / 0 °C

3: 62 percent / DBU / CH₂Cl₂ / 1 h / 0 - 20 °C

4: 95 percent / NaOH / methanol; H₂O / 20 h / Heating

With sodium hydroxide; potassium carbonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium iodide; In methanol; dichloromethane; water; acetone;

DOI:10.1021/ol0627202

upstream raw materials:

O-methylresorcine

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

Downstream raw materials:

tert-butyl (1R,2R)-1-(2-allyloxy-4-methoxyphenyl)-1,3-dihydroxypropan-2-ylcarbamate

tert-butyl (4S,5S)-4-(2-allyloxy-4-methoxyphenyl)-2-trichloromethyl-5,6-dihydro-4H-1,3-oxazin-5-ylcarbamate