(4S,5R)-3-<(R)-5,6-(Isopropylidenedioxy)hexanoyl>-4-methyl-5-phenyl-1,3-oxazolidin-2-one

Base Information

• Chemical Name: (4S,5R)-3-<(R)-5,6-(Isopropylidenedioxy)hexanoyl>-4-methyl-5-phenyl-1,3-oxazolidin-2-one
• CAS No.: 130258-52-5
• Molecular Formula: C₁₉H₂₅NO₅
• Molecular Weight: 347.411
• Mol file: 130258-52-5.mol

Synonyms:(4S,5R)-3-<(R)-5,6-(Isopropylidenedioxy)hexanoyl>-4-methyl-5-phenyl-1,3-oxazolidin-2-one

Chemical Property of (4S,5R)-3-<(R)-5,6-(Isopropylidenedioxy)hexanoyl>-4-methyl-5-phenyl-1,3-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R)-3-<(R)-5,6-(Isopropylidenedioxy)hexanoyl>-4-methyl-5-phenyl-1,3-oxazolidin-2-one

There total 5 articles about (4S,5R)-3-<(R)-5,6-(Isopropylidenedioxy)hexanoyl>-4-methyl-5-phenyl-1,3-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: 70.0%

(4S,5R)-4-methyl-5-phenyl-oxazolidin-2-one (16251-45-9,17097-67-5,28044-22-6,28044-23-7,39663-75-7,54418-69-8,77943-39-6,125133-96-2,149055-02-7) + (R)-4-(2,2-dimethyl-1,3-dioxolan-4-yl)butyric acid (142560-61-0) → (4S,5R)-3-<(R)-5,6-(Isopropylidenedioxy)hexanoyl>-4-methyl-5-phenyl-1,3-oxazolidin-2-one (130258-52-5)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; Ambient temperature;

DOI:10.1248/cpb.38.1781

Reference yield:

methyl (R)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)acetate (112031-10-4) → (4S,5R)-3-<(R)-5,6-(Isopropylidenedioxy)hexanoyl>-4-methyl-5-phenyl-1,3-oxazolidin-2-one (130258-52-5)

Guidance literature:

Multi-step reaction with 5 steps

1: DIBALH / hexane; diethyl ether / 0.08 h / -70 °C

2: acetonitrile / 1 h / Heating

3: 97 percent / H₂ / 10percent Pd/C / ethyl acetate / 4 h / 760 Torr

4: 13.7 g / KOH / methanol; H₂O / 0.5 h / Ambient temperature

5: 20.3 g / DCC, DMAP / CH₂Cl₂ / 1) r.t., 1 d, 2) reflux, 2.5 h

With dmap; potassium hydroxide; hydrogen; diisobutylaluminium hydride; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; diethyl ether; hexane; dichloromethane; water; ethyl acetate; acetonitrile;

DOI:10.1021/jo00036a026

Reference yield:

((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-acetaldehyde (72496-37-8) → (4S,5R)-3-<(R)-5,6-(Isopropylidenedioxy)hexanoyl>-4-methyl-5-phenyl-1,3-oxazolidin-2-one (130258-52-5)

Guidance literature:

Multi-step reaction with 4 steps

1: acetonitrile / 1 h / Heating

2: 97 percent / H₂ / 10percent Pd/C / ethyl acetate / 4 h / 760 Torr

3: 13.7 g / KOH / methanol; H₂O / 0.5 h / Ambient temperature

4: 20.3 g / DCC, DMAP / CH₂Cl₂ / 1) r.t., 1 d, 2) reflux, 2.5 h

With dmap; potassium hydroxide; hydrogen; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; dichloromethane; water; ethyl acetate; acetonitrile;

DOI:10.1021/jo00036a026

upstream raw materials:

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

(R)-4-(2,2-dimethyl-1,3-dioxolan-4-yl)butyric acid

((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-acetaldehyde

(R)-2,2-Dimethyl-1,3-dioxolane-4-butanoic acid, methyl ester

Downstream raw materials:

(Z)-3-[(1R,2R,3S)-2-((R)-Cyano-methyl-methyl)-3-methyl-cyclohexyl]-2-((2S,3S,6R)-6-{(E)-3-[(2S,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-propenyl}-3-methyl-tetrahydro-pyran-2-yl)-acrylic acid methyl ester

(E)-3-[(1R,2R,3S)-2-((R)-Cyano-methyl-methyl)-3-methyl-cyclohexyl]-2-((2S,3S,6R)-6-{(E)-3-[(2S,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-propenyl}-3-methyl-tetrahydro-pyran-2-yl)-acrylic acid methyl ester

C₄₁H₆₈O₈Si

4-Methoxy-3-((R)-2-{(1R,2R,6S)-2-[(E)-2-((2S,3S,6R)-6-{(E)-3-[(2S,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-propenyl}-3-methyl-tetrahydro-pyran-2-yl)-3-triethylsilanyloxy-propenyl]-6-methyl-cyclohexyl}-propionyl)-5-methylene-5H-furan-2-one