(S)-4-Benzyl-3-((R)-2-methyl-4-trimethylsilanylmethyl-pent-4-enoyl)-oxazolidin-2-one

Base Information

• Chemical Name: (S)-4-Benzyl-3-((R)-2-methyl-4-trimethylsilanylmethyl-pent-4-enoyl)-oxazolidin-2-one
• CAS No.: 866148-29-0
• Molecular Formula: C₂₀H₂₉NO₃Si
• Molecular Weight: 359.541
• Mol file: 866148-29-0.mol

Synonyms:(S)-4-Benzyl-3-((R)-2-methyl-4-trimethylsilanylmethyl-pent-4-enoyl)-oxazolidin-2-one

Chemical Property of (S)-4-Benzyl-3-((R)-2-methyl-4-trimethylsilanylmethyl-pent-4-enoyl)-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-Benzyl-3-((R)-2-methyl-4-trimethylsilanylmethyl-pent-4-enoyl)-oxazolidin-2-one

There total 2 articles about (S)-4-Benzyl-3-((R)-2-methyl-4-trimethylsilanylmethyl-pent-4-enoyl)-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: 87.0%

2-(trimethylsilyl)methylallyl iodide (80121-73-9) + (S)-4-benzyl-3-propionyl-2-oxazolidinone (131685-53-5,101711-78-8) → (S)-4-Benzyl-3-((R)-2-methyl-4-trimethylsilanylmethyl-pent-4-enoyl)-oxazolidin-2-one (866148-29-0)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 - 10 ℃; for 4.16667h;

DOI:10.1021/ol051544e

Reference yield:

2-chloromethyl-3-trimethylsilyl-1-propene (18388-03-9) → (S)-4-Benzyl-3-((R)-2-methyl-4-trimethylsilanylmethyl-pent-4-enoyl)-oxazolidin-2-one (866148-29-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium iodide / acetone / 16 h / 20 °C / Darkness

2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.33 h / -78 °C / Inert atmosphere

2.2: 4.17 h / -78 - 10 °C / Inert atmosphere

With sodium hexamethyldisilazane; sodium iodide; In tetrahydrofuran; acetone;

DOI:10.1021/jo3026077

Reference yield:

(S)-4-Benzyl-3-((R)-2-methyl-4-trimethylsilanylmethyl-pent-4-enoyl)-oxazolidin-2-one (866148-29-0) → 7-(3,4-dihydroxy-1-methyl-4-phenyl-1-triethylsilanyloxy-butyl)-3-methyl-5-methylene-oct-7-enenitrile (866148-39-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 99 percent / LiBH₄ / methanol; tetrahydrofuran / 0 - 20 °C

2.1: 99 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: 65 percent / TiCl₄ / CH₂Cl₂ / 0.25 h / -78 °C

4.1: SOCl₂; pyridine / toluene / 0.5 h / -78 °C

4.2: TBAF / tetrahydrofuran / 0 - 20 °C

5.1: 81 percent / PPh₃; DEAD / diethyl ether; toluene / 0 - 20 °C

6.1: 77 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

7.1: MeSO₂NH₂; (DHQD)2PHAL; K₂OsO₄*2H₂O / K₂CO₃; K₃Fe(CN)6 / H₂O; 2-methyl-propan-2-ol / 16 h

With pyridine; potassium osmate(VI); lithium borohydride; thionyl chloride; methanesulfonamide; titanium tetrachloride; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; triphenylphosphine; diethylazodicarboxylate; potassium carbonate; potassium hexacyanoferrate(III); In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; tert-butyl alcohol; 5.1: Mitsunobu reaction / 7.1: Sharpless dihydroxylation;

DOI:10.1021/ol051544e

upstream raw materials:

2-(trimethylsilyl)methylallyl iodide

(S)-4-benzyl-3-propionyl-2-oxazolidinone

2-chloromethyl-3-trimethylsilyl-1-propene

Downstream raw materials:

(5E,9E)-(2R,7R)-2,6,7-Trimethyl-4-methylene-10-phenyl-deca-5,9-diene-1,7-diol

(E)-(2R,7R)-2,7-Dimethyl-4,6-dimethylene-10-phenyl-dec-9-ene-1,7-diol

(6E,10E)-(3R,8R)-8-Hydroxy-3,7,8-trimethyl-5-methylene-11-phenyl-undeca-6,10-dienenitrile

(E)-(3R,8R)-8-Hydroxy-3,8-dimethyl-5,7-dimethylene-11-phenyl-undec-10-enenitrile