(S)-4-Benzyl-3-((4aR,6S,9aS)-2,9,9-trimethyl-5-oxo-4,4a,5,6,7,8,9,9a-octahydro-3H-benzocycloheptene-6-carbonyl)-oxazolidin-2-one

Base Information

• Chemical Name: (S)-4-Benzyl-3-((4aR,6S,9aS)-2,9,9-trimethyl-5-oxo-4,4a,5,6,7,8,9,9a-octahydro-3H-benzocycloheptene-6-carbonyl)-oxazolidin-2-one
• CAS No.: 198699-85-3
• Molecular Formula: C₂₅H₃₁NO₄
• Molecular Weight: 409.525
• Mol file: 198699-85-3.mol

Synonyms:

Chemical Property of (S)-4-Benzyl-3-((4aR,6S,9aS)-2,9,9-trimethyl-5-oxo-4,4a,5,6,7,8,9,9a-octahydro-3H-benzocycloheptene-6-carbonyl)-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-Benzyl-3-((4aR,6S,9aS)-2,9,9-trimethyl-5-oxo-4,4a,5,6,7,8,9,9a-octahydro-3H-benzocycloheptene-6-carbonyl)-oxazolidin-2-one

There total 3 articles about (S)-4-Benzyl-3-((4aR,6S,9aS)-2,9,9-trimethyl-5-oxo-4,4a,5,6,7,8,9,9a-octahydro-3H-benzocycloheptene-6-carbonyl)-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:

(S)-1-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-((E)-3,3,6-trimethyl-hepta-4,6-dienyl)-pent-4-ene-1,3-dione (198699-84-2) → (S)-4-Benzyl-3-((S)-2,9,9-trimethyl-5-oxo-4,4a,5,6,7,8,9,9a-octahydro-3H-benzocycloheptene-6-carbonyl)-oxazolidin-2-one + (S)-4-Benzyl-3-((4aR,6S,9aS)-2,9,9-trimethyl-5-oxo-4,4a,5,6,7,8,9,9a-octahydro-3H-benzocycloheptene-6-carbonyl)-oxazolidin-2-one (198699-85-3)

Guidance literature:

With zinc dibromide; In dichloromethane; at 0 ℃; for 1.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1002/anie.199721191

Reference yield:

[4S,3(6E)]-4-Benzyl-3-(5,5,8-trimethylnona-6,8-dienoyl)-2-oxazolidinone (290812-17-8) → (S)-4-Benzyl-3-((4aR,6S,9aS)-2,9,9-trimethyl-5-oxo-4,4a,5,6,7,8,9,9a-octahydro-3H-benzocycloheptene-6-carbonyl)-oxazolidin-2-one (198699-85-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) Bu₂BOTf, (i-Pr)2NEt, isoprene / 1.) 0 deg C, 2.) -78 deg C

2: SO₃*pyridne, (i-Pr)2NEt / CH₂Cl₂; dimethylsulfoxide / -10 °C

3: ZnBr₂ / CH₂Cl₂ / 1.5 h / 0 °C

With pyridine-SO₃ complex; di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; zinc dibromide; isoprene; In dichloromethane; dimethyl sulfoxide;

DOI:10.1002/anie.199721191

Reference yield:

(S)-4-Benzyl-3-[(E)-(S)-2-((R)-1-hydroxy-allyl)-5,5,8-trimethyl-nona-6,8-dienoyl]-oxazolidin-2-one (198699-83-1) → (S)-4-Benzyl-3-((4aR,6S,9aS)-2,9,9-trimethyl-5-oxo-4,4a,5,6,7,8,9,9a-octahydro-3H-benzocycloheptene-6-carbonyl)-oxazolidin-2-one (198699-85-3)

Guidance literature:

Multi-step reaction with 2 steps

1: SO₃*pyridne, (i-Pr)2NEt / CH₂Cl₂; dimethylsulfoxide / -10 °C

2: ZnBr₂ / CH₂Cl₂ / 1.5 h / 0 °C

With pyridine-SO₃ complex; N-ethyl-N,N-diisopropylamine; zinc dibromide; In dichloromethane; dimethyl sulfoxide;

DOI:10.1002/anie.199721191

upstream raw materials:

(S)-1-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-((E)-3,3,6-trimethyl-hepta-4,6-dienyl)-pent-4-ene-1,3-dione

[4S,3(6E)]-4-Benzyl-3-(5,5,8-trimethylnona-6,8-dienoyl)-2-oxazolidinone

(S)-4-Benzyl-3-[(E)-(S)-2-((R)-1-hydroxy-allyl)-5,5,8-trimethyl-nona-6,8-dienoyl]-oxazolidin-2-one