(S)-3-((S,E)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpent-2-enoyl)-isopropyloxazolidin-2-one

Base Information

• Chemical Name: (S)-3-((S,E)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpent-2-enoyl)-isopropyloxazolidin-2-one
• CAS No.: 1297531-60-2
• Molecular Formula: C₂₈H₃₇NO₄Si
• Molecular Weight: 479.692
• Mol file: 1297531-60-2.mol

Synonyms:(S)-3-((S,E)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpent-2-enoyl)-isopropyloxazolidin-2-one

Chemical Property of (S)-3-((S,E)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpent-2-enoyl)-isopropyloxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-((S,E)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpent-2-enoyl)-isopropyloxazolidin-2-one

There total 1 articles about (S)-3-((S,E)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpent-2-enoyl)-isopropyloxazolidin-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: 83.0%

(R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropanal (91751-24-5,92817-88-4,123284-89-9,112897-04-8) + diethyl 2-[(4S)-4-(1-methylethyl)-2-oxo-3-oxazolidinyl]-2-oxoethanephosphonate (147122-00-7) → (S)-3-((S,E)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpent-2-enoyl)-isopropyloxazolidin-2-one (1297531-60-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; lithium chloride; In acetonitrile; for 16h; Inert atmosphere;

DOI:10.1021/ol200834p

Reference yield: 100.0%

(S)-3-((S,E)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpent-2-enoyl)-isopropyloxazolidin-2-one (1297531-60-2) → (S)-3-((S)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpentanoyl)-4-isopropyloxazolidin-2-one (1297531-42-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethyl acetate; for 24h;

DOI:10.1021/ol200834p

Reference yield:

(S)-3-((S,E)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpent-2-enoyl)-isopropyloxazolidin-2-one (1297531-60-2) → (1S,2S,6S,8S,Z)-1-(3,5-bis((triisopropylsilyl)oxy)phenyl)-10-cyclohexyl-1-hydroxy-2,6,8-trimethyldec-9-en-5-one (1297531-49-7)

Guidance literature:

Multi-step reaction with 14 steps

1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 24 h

2: lithium hexamethyldisilazane / tetrahydrofuran / 6.17 h / -78 - 0 °C / Inert atmosphere

3: lithium borohydride / tetrahydrofuran; water / 6 h / 0 °C

4: CSA / dichloromethane / 24 h / 20 °C

5: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C

6: C₅H₅N*HO₃S; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 °C

7: chromium dichloride; nickel dichloride / tetrahydrofuran; dimethyl sulfoxide / 17 h / 20 °C / Inert atmosphere; Large scale reaction

8: 2,6-dimethylpyridine / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere

9: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 2 h / 0 °C

10: 1H-imidazole; iodine; triphenylphosphine / diethyl ether; acetonitrile / 20 °C / Darkness

11: lithium carbonate / acetonitrile; benzene / 60 h / Reflux

12: lithium hexamethyldisilazane / tetrahydrofuran; toluene / -78 - 0 °C / Inert atmosphere

13: pyridinium p-toluenesulfonate / methanol; dichloromethane / 2.5 h / 20 °C

14: tris(triphenylphosphine)ruthenium(II) chloride; methyllithium / tetrahydrofuran; diethyl ether / 4.7 h / 20 - 60 °C / Inert atmosphere

With 1H-imidazole; 2,6-dimethylpyridine; chromium dichloride; lithium borohydride; tris(triphenylphosphine)ruthenium(II) chloride; palladium 10% on activated carbon; C₅H₅N*HO₃S; tetrabutyl ammonium fluoride; water; methyllithium; hydrogen; iodine; pyridinium p-toluenesulfonate; lithium carbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel dichloride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; toluene; acetonitrile; benzene; 7: Nozaki-Hiyama-Kishi reaction;

DOI:10.1021/ol200834p

upstream raw materials:

(R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropanal

diethyl 2-[(4S)-4-(1-methylethyl)-2-oxo-3-oxazolidinyl]-2-oxoethanephosphonate

Downstream raw materials:

(2S,4S)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentan-1-ol

tert-butyl(((2S,4S)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentyl)oxy)diphenylsilane

(2S,4S)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentanal

C₅₀H₉₀O₆Si₃