(4R)-3-((2R,3S,5S,7S)-2-hydroxy-3,5,7-trimethyldecanoyl)-4-phenyloxazolidin-2-one

Base Information

• Chemical Name: (4R)-3-((2R,3S,5S,7S)-2-hydroxy-3,5,7-trimethyldecanoyl)-4-phenyloxazolidin-2-one
• CAS No.: 749228-69-1
• Molecular Formula: C₂₂H₃₃NO₄
• Molecular Weight: 375.508
• Mol file: 749228-69-1.mol

Synonyms:

Chemical Property of (4R)-3-((2R,3S,5S,7S)-2-hydroxy-3,5,7-trimethyldecanoyl)-4-phenyloxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R)-3-((2R,3S,5S,7S)-2-hydroxy-3,5,7-trimethyldecanoyl)-4-phenyloxazolidin-2-one

There total 8 articles about (4R)-3-((2R,3S,5S,7S)-2-hydroxy-3,5,7-trimethyldecanoyl)-4-phenyloxazolidin-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:

(4R)-3-((3S,5S,7S)-3,5,7-trimethyldecanoyl)-4-phenyloxazolidin-2-one (749228-67-9) → (4R)-3-((2R,3S,5S,7S)-2-hydroxy-3,5,7-trimethyldecanoyl)-4-phenyloxazolidin-2-one (749228-69-1) + (4R)-3-((2S,3S,5S,7S)-2-hydroxy-3,5,7-trimethyldecanoyl)-4-phenyloxazolidin-2-one

Guidance literature:

(4R)-3-((3S,5S,7S)-3,5,7-trimethyldecanoyl)-4-phenyloxazolidin-2-one; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h;

With camphor-10-sulfonic acid; (+)-[(8,8-dichlorocamphoryl)sulfonyl]oxaziridine; In tetrahydrofuran;

DOI:10.1021/jo049567e

Reference yield:

(3S)-3-methylhexanal (110065-42-4) → (4R)-3-((2R,3S,5S,7S)-2-hydroxy-3,5,7-trimethyldecanoyl)-4-phenyloxazolidin-2-one (749228-69-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: CH₂Cl₂ / 24 h

2.1: CuBr*Me₂S / diethyl ether / 1 h / -40 °C

2.2: 89 percent / BF₃*Et₂O / diethyl ether; tetrahydrofuran / 21 h / -78 - -20 °C

3.1: 90 percent / LiBH₄; MeOH / diethyl ether / 1 h / -10 - 20 °C

4.1: NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 2.5 h / 20 °C

5.1: CH₂Cl₂ / 24 h

5.2: 82 percent / I₂ / CH₂Cl₂ / 48 h

6.1: CuBr*Me₂S / diethyl ether / 1 h / -40 °C

6.2: 86 percent / BF₃*Et₂O / diethyl ether; tetrahydrofuran / 21 h / -78 - -20 °C

7.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C

7.2: Davis oxaziridine; camphorsulfonic acid / tetrahydrofuran

With methanol; lithium borohydride; copper(I) bromide dimethylsulfide complex; sodium hexamethyldisilazane; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: Wittig reaction / 4.1: Dess-Martin oxidation / 5.1: Wittig reaction;

DOI:10.1021/jo049567e

Reference yield:

(4S)-3-(3-methylhexanoyl)-4-phenyloxazolidin-2-one → (4R)-3-((2R,3S,5S,7S)-2-hydroxy-3,5,7-trimethyldecanoyl)-4-phenyloxazolidin-2-one (749228-69-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: LiBH₄; MeOH / diethyl ether / 1 h / -20 - 20 °C

2.1: NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 2.5 h / 20 °C

3.1: CH₂Cl₂ / 24 h

4.1: CuBr*Me₂S / diethyl ether / 1 h / -40 °C

4.2: 89 percent / BF₃*Et₂O / diethyl ether; tetrahydrofuran / 21 h / -78 - -20 °C

5.1: 90 percent / LiBH₄; MeOH / diethyl ether / 1 h / -10 - 20 °C

6.1: NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 2.5 h / 20 °C

7.1: CH₂Cl₂ / 24 h

7.2: 82 percent / I₂ / CH₂Cl₂ / 48 h

8.1: CuBr*Me₂S / diethyl ether / 1 h / -40 °C

8.2: 86 percent / BF₃*Et₂O / diethyl ether; tetrahydrofuran / 21 h / -78 - -20 °C

9.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C

9.2: Davis oxaziridine; camphorsulfonic acid / tetrahydrofuran

With methanol; lithium borohydride; copper(I) bromide dimethylsulfide complex; sodium hexamethyldisilazane; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; diethyl ether; dichloromethane; 2.1: Dess-Martin oxidation / 3.1: Wittig reaction / 6.1: Dess-Martin oxidation / 7.1: Wittig reaction;

DOI:10.1021/jo049567e

upstream raw materials:

(4R)-3-((3S,5S,7S)-3,5,7-trimethyldecanoyl)-4-phenyloxazolidin-2-one

(4R)-3-((5S,7S)-(2E)-5,7-dimethyldec-2-enoyl)-4-phenyloxazolidin-2-one

(3S)-3-methylhexanal

(3S,5S)-3,5-dimethyloctanal