(4S-trans)-4-(cyclohexylmethyl)-5-(2-furanyl)-2-oxazolidinone

Base Information

• Chemical Name: (4S-trans)-4-(cyclohexylmethyl)-5-(2-furanyl)-2-oxazolidinone
• CAS No.: 133660-33-0
• Molecular Formula: C₁₄H₁₉NO₃
• Molecular Weight: 249.31
• Mol file: 133660-33-0.mol

Synonyms:(4S-trans)-4-(cyclohexylmethyl)-5-(2-furanyl)-2-oxazolidinone

Chemical Property of (4S-trans)-4-(cyclohexylmethyl)-5-(2-furanyl)-2-oxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S-trans)-4-(cyclohexylmethyl)-5-(2-furanyl)-2-oxazolidinone

There total 6 articles about (4S-trans)-4-(cyclohexylmethyl)-5-(2-furanyl)-2-oxazolidinone 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:

(S)-2-tert-butoxycarbonylamino-3-cyclohexylpropionic acid (37736-82-6) → (4S-trans)-4-(cyclohexylmethyl)-5-(2-furanyl)-2-oxazolidinone (133660-33-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) imidazole, phenyl dichlorophosphate / 1.) CH₂Cl₂, 0 deg C, 1 h, 2.) CH₂Cl₂, overnight

2: 1.) secondary butyllithium / 1.) THF, hexane, -78 deg C, 1.5 h, 2.) THF, hexane, 0 deg C, 1 h

3: 95 percent / NaBH₄ / tetrahydrofuran; methanol / 1.5 h / 0 °C

4: trifluoroacetic acid / CH₂Cl₂ / 2 h / Ambient temperature

With 1H-imidazole; sodium tetrahydroborate; sec.-butyllithium; O-phenyl phosphorodichloridate; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane;

Reference yield:

(S)-α-[[(1,1-dimethylethoxy)carbonyl]amino]-N-methoxy-N-methylcyclohexanepropanamide (115766-13-7) → (4S-trans)-4-(cyclohexylmethyl)-5-(2-furanyl)-2-oxazolidinone (133660-33-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) secondary butyllithium / 1.) THF, hexane, -78 deg C, 1.5 h, 2.) THF, hexane, 0 deg C, 1 h

2: 95 percent / NaBH₄ / tetrahydrofuran; methanol / 1.5 h / 0 °C

3: trifluoroacetic acid / CH₂Cl₂ / 2 h / Ambient temperature

With sodium tetrahydroborate; sec.-butyllithium; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane;

Reference yield:

1,1-dimethylethyl <(S)1-cyclohexylmethyl-(R,S)2-(2-furanyl)-2-hydroxyethyl>carbamate → (4S-cis)-4-cyclohexylmethyl-5-(2-furanyl)-2-oxazolidinone (141258-96-0) + (4S-trans)-4-(cyclohexylmethyl)-5-(2-furanyl)-2-oxazolidinone (133660-33-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 2h; Yields of byproduct given; Ambient temperature;

upstream raw materials:

2-lithiofuran

(S)-2-(t-butoxycarbonylamino)-3-cyclohexyl-1-propanal

(S)-2-tert-butoxycarbonylamino-3-cyclohexylpropionic acid

(S)-α-[[(1,1-dimethylethoxy)carbonyl]amino]-N-methoxy-N-methylcyclohexanepropanamide

Downstream raw materials:

(4S-trans)4-(cyclohexylmethyl)-5-(5-acetyl-2-furan-yl)-2-oxazolidinone

Thioacetic acid S-[(R)-4-((4S,5R)-4-cyclohexylmethyl-2-oxo-oxazolidin-5-yl)-4-methanesulfonyloxy-butyl] ester

Thioacetic acid S-[(S)-4-((4S,5R)-4-cyclohexylmethyl-2-oxo-oxazolidin-5-yl)-4-methanesulfonyloxy-butyl] ester

2-carboxyamino-1-cyclohexyl-1,2,5,6-tetradeoxy-7-thio-L-arabino-heptitol-7-acetate, intramol-2,3-ester