(4S)-4-ethenyl-3-[(1R)-1-(1-hydroxycyclohexyl)but-3-en-1-yl]-1,3-oxazolidin-2-one

Base Information

• Chemical Name: (4S)-4-ethenyl-3-[(1R)-1-(1-hydroxycyclohexyl)but-3-en-1-yl]-1,3-oxazolidin-2-one
• CAS No.: 1416449-24-5
• Molecular Formula: C₁₅H₂₃NO₃
• Molecular Weight: 265.353
• Mol file: 1416449-24-5.mol

Synonyms:(4S)-4-ethenyl-3-[(1R)-1-(1-hydroxycyclohexyl)but-3-en-1-yl]-1,3-oxazolidin-2-one

Chemical Property of (4S)-4-ethenyl-3-[(1R)-1-(1-hydroxycyclohexyl)but-3-en-1-yl]-1,3-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S)-4-ethenyl-3-[(1R)-1-(1-hydroxycyclohexyl)but-3-en-1-yl]-1,3-oxazolidin-2-one

There total 2 articles about (4S)-4-ethenyl-3-[(1R)-1-(1-hydroxycyclohexyl)but-3-en-1-yl]-1,3-oxazolidin-2-one 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: 57.0%

(4S)-3-[(1S)-1-tributylstannylbut-3-en-1-yl]-4-ethenyl-1,3-oxazolidin-2-one (1416449-18-7,1416449-21-2) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → (4S)-4-ethenyl-3-[(1S)-1-(1-hydroxycyclohexyl)but-3-en-1-yl]-1,3-oxazolidin-2-one (1416449-23-4) + (4S)-4-ethenyl-3-[(1R)-1-(1-hydroxycyclohexyl)but-3-en-1-yl]-1,3-oxazolidin-2-one (1416449-24-5)

Guidance literature:

(4S)-3-[(1S)-1-tributylstannylbut-3-en-1-yl]-4-ethenyl-1,3-oxazolidin-2-one; With n-butyllithium; In tetrahydrofuran; at -100 ℃; for 0.0833333h; Inert atmosphere; Schlenk technique;

cyclohexanone; In tetrahydrofuran; at -100 ℃; Overall yield = 77 %; Inert atmosphere; Schlenk technique;

DOI:10.1021/ol303213r

Reference yield:

methyl [(1S)-1-tributylstannylbut-3-en-1-yl][(2S)-1-hydroxybut-3-en-2-yl]carbamate (1416449-13-2,1416449-15-4) → (4S)-4-ethenyl-3-[(1S)-1-(1-hydroxycyclohexyl)but-3-en-1-yl]-1,3-oxazolidin-2-one (1416449-23-4) + (4S)-4-ethenyl-3-[(1R)-1-(1-hydroxycyclohexyl)but-3-en-1-yl]-1,3-oxazolidin-2-one (1416449-24-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.75 h / 20 °C

2.1: n-butyllithium / tetrahydrofuran / 0.08 h / -100 °C / Inert atmosphere; Schlenk technique

2.2: -100 °C / Inert atmosphere; Schlenk technique

With n-butyllithium; sodium hydride; In tetrahydrofuran; mineral oil;

DOI:10.1021/ol303213r

Reference yield: 89.0%

(4S)-4-ethenyl-3-[(1R)-1-(1-hydroxycyclohexyl)but-3-en-1-yl]-1,3-oxazolidin-2-one (1416449-24-5) → (5R,8aS)-5-(1-hydroxycyclohexyl)-1,5,6,8a-tetrahydro[1,3]oxazolo[3,4-a]pyridin-3-one (1416449-31-4)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 40 ℃; for 1h;

DOI:10.1002/adsc.201900349

upstream raw materials:

methyl [(1S)-1-tributylstannylbut-3-en-1-yl][(2S)-1-hydroxybut-3-en-2-yl]carbamate

(4S)-3-[(1S)-1-tributylstannylbut-3-en-1-yl]-4-ethenyl-1,3-oxazolidin-2-one

cyclohexanone

Downstream raw materials:

(5R,8aS)-5-(1-hydroxycyclohexyl)-1,5,6,8a-tetrahydro[1,3]oxazolo[3,4-a]pyridin-3-one