3-[5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2-methyl-pentanoyl]-4-methyl-5-phenyl-oxazolidin-2-one

Base Information

• Chemical Name: 3-[5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2-methyl-pentanoyl]-4-methyl-5-phenyl-oxazolidin-2-one
• CAS No.: 919608-28-9
• Molecular Formula: C₂₁H₂₉NO₆
• Molecular Weight: 391.464
• Mol file: 919608-28-9.mol

Synonyms:3-[5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2-methyl-pentanoyl]-4-methyl-5-phenyl-oxazolidin-2-one

Chemical Property of 3-[5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2-methyl-pentanoyl]-4-methyl-5-phenyl-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2-methyl-pentanoyl]-4-methyl-5-phenyl-oxazolidin-2-one

There total 1 articles about 3-[5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2-methyl-pentanoyl]-4-methyl-5-phenyl-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: 84.0%

(4S)-4,5-(isopropylidenedioxy)-1-pentanal (42890-81-3) + (4S,5R)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one (77877-20-4,116382-72-0,143654-01-7) → 3-[5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2-methyl-pentanoyl]-4-methyl-5-phenyl-oxazolidin-2-one (919608-28-9)

Guidance literature:

(4S,5R)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one; With di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane; at -40 - 0 ℃;

(4S)-4,5-(isopropylidenedioxy)-1-pentanal; In dichloromethane; at -78 - 0 ℃; for 4.8h;

DOI:10.1002/anie.200602860

Reference yield:

3-[5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2-methyl-pentanoyl]-4-methyl-5-phenyl-oxazolidin-2-one (919608-28-9) → C40H58O7Si (919608-24-5)

Guidance literature:

Multi-step reaction with 12 steps

1.1: lithium borohydride / diethyl ether; tetrahydrofuran / 0 - 20 °C

2.1: 3.59 g / imidazole / CH₂Cl₂ / 1 h / 20 °C

3.1: 98 percent / TEA / CH₂Cl₂ / 0 - 20 °C

4.1: 84 percent / CSA; methanol / 2 h / 20 °C

5.1: 80 percent / sodium hexamethyldisilazide / tetrahydrofuran / 0 - 20 °C

6.1: 89 percent / SO₃*pyridine; TEA; DMSO / CH₂Cl₂ / 0.5 h / 20 °C

7.1: 557 mg / tetrahydrofuran; hexane / -78 - 20 °C

8.1: 85 percent / m-CPBA / CH₂Cl₂ / 3 h

9.1: lithium aluminum hydride / diethyl ether / 12 h

9.2: 30 mg / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

10.1: 99 percent / NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 2 h / 20 °C

11.1: 95 percent / imidazole; DMAP / CH₂Cl₂ / 2 h / 20 °C

12.1: 93 percent / hydrogen / Pd(OH)2/C / ethyl acetate / 1 h

With 1H-imidazole; methanol; dmap; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; lithium borohydride; 2-methyl-but-2-ene; pyridine-SO₃ complex; TEA; camphor-10-sulfonic acid; hydrogen; sodium hexamethyldisilazane; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; palladium dihydroxide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; ethyl acetate; tert-butyl alcohol; 5.1: Williamson ether synthesis / 7.1: Wittig olefination / 9.2: Dess-Martin oxidation;

DOI:10.1016/j.tet.2007.07.005

Reference yield:

3-[5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2-methyl-pentanoyl]-4-methyl-5-phenyl-oxazolidin-2-one (919608-28-9) → 2-[5-(3-{5-[2-benzyloxy-3-(5-methyl-tetrahydro-furan-2-yl)-butyl]-tetrahydro-furan-2-yl}-2-oxo-butyl)-tetrahydro-furan-2-yl]-propionaldehyde (919608-44-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: lithium borohydride / diethyl ether; tetrahydrofuran / 0 - 20 °C

2.1: 3.59 g / imidazole / CH₂Cl₂ / 1 h / 20 °C

3.1: 98 percent / TEA / CH₂Cl₂ / 0 - 20 °C

4.1: 84 percent / CSA; methanol / 2 h / 20 °C

5.1: 80 percent / sodium hexamethyldisilazide / tetrahydrofuran / 0 - 20 °C

6.1: 89 percent / SO₃*pyridine; TEA; DMSO / CH₂Cl₂ / 0.5 h / 20 °C

7.1: 557 mg / tetrahydrofuran; hexane / -78 - 20 °C

8.1: 85 percent / m-CPBA / CH₂Cl₂ / 3 h

9.1: lithium aluminum hydride / diethyl ether / 12 h

9.2: 30 mg / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

With 1H-imidazole; methanol; lithium aluminium tetrahydride; lithium borohydride; pyridine-SO₃ complex; TEA; camphor-10-sulfonic acid; sodium hexamethyldisilazane; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 5.1: Williamson ether synthesis / 7.1: Wittig olefination / 9.2: Dess-Martin oxidation;

DOI:10.1016/j.tet.2007.07.005

upstream raw materials:

(4S)-4,5-(isopropylidenedioxy)-1-pentanal

(4S,5R)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one

Downstream raw materials:

3-benzyloxy-4-(5-methyl-tetrahydro-furan-2-yl)-pentanal

2-(2-benzyloxy-1-methyl-pent-4-enyl)-5-methyl-tetrahydro-furan

5-benzyloxy-3-hydroxy-6-(5-methyl-tetrahydro-furan-2-yl)-heptanal

6-benzyloxy-7-(5-methyl-tetrahydro-furan-2-yl)-oct-1-en-4-ol