(4R,5S)-3-((S)-3-((4R,5S)-2,2-dimethyl-5-(prop-1-en-2-yl)-1,3-dioxolan-4-yl)-3-hydroxy-2,2-dimethylpropanoyl)-5-methyl-4-phenyloxazolidin-2-one

Base Information

• Chemical Name: (4R,5S)-3-((S)-3-((4R,5S)-2,2-dimethyl-5-(prop-1-en-2-yl)-1,3-dioxolan-4-yl)-3-hydroxy-2,2-dimethylpropanoyl)-5-methyl-4-phenyloxazolidin-2-one
• CAS No.: 1453081-98-5
• Molecular Formula: C₂₃H₃₁NO₆
• Molecular Weight: 417.502
• Mol file: 1453081-98-5.mol

Synonyms:(4R,5S)-3-((S)-3-((4R,5S)-2,2-dimethyl-5-(prop-1-en-2-yl)-1,3-dioxolan-4-yl)-3-hydroxy-2,2-dimethylpropanoyl)-5-methyl-4-phenyloxazolidin-2-one

Chemical Property of (4R,5S)-3-((S)-3-((4R,5S)-2,2-dimethyl-5-(prop-1-en-2-yl)-1,3-dioxolan-4-yl)-3-hydroxy-2,2-dimethylpropanoyl)-5-methyl-4-phenyloxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S)-3-((S)-3-((4R,5S)-2,2-dimethyl-5-(prop-1-en-2-yl)-1,3-dioxolan-4-yl)-3-hydroxy-2,2-dimethylpropanoyl)-5-methyl-4-phenyloxazolidin-2-one

There total 9 articles about (4R,5S)-3-((S)-3-((4R,5S)-2,2-dimethyl-5-(prop-1-en-2-yl)-1,3-dioxolan-4-yl)-3-hydroxy-2,2-dimethylpropanoyl)-5-methyl-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: 68.0%

(4R,5S)-3-(2-bromo-2-methylpropanoyl)-5-methyl-4-phenyloxazolidin-2-one (1453081-86-1) + (4S,5S)-2,2-dimethyl-5-(prop-1-en-2-yl)-1,3-dioxolane-4-carbaldehyde (1453081-97-4) → (4R,5S)-3-((S)-3-((4R,5S)-2,2-dimethyl-5-(prop-1-en-2-yl)-1,3-dioxolan-4-yl)-3-hydroxy-2,2-dimethylpropanoyl)-5-methyl-4-phenyloxazolidin-2-one (1453081-98-5)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere; Schlenk technique;

DOI:10.1002/ejoc.201300148

Reference yield:

(4R,5S)-5-methyl-4-phenyloxazolidin-2-one (638211-38-8) → (4R,5S)-3-((S)-3-((4R,5S)-2,2-dimethyl-5-(prop-1-en-2-yl)-1,3-dioxolan-4-yl)-3-hydroxy-2,2-dimethylpropanoyl)-5-methyl-4-phenyloxazolidin-2-one (1453081-98-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran / 20 °C / Inert atmosphere

1.2: 2 h / -40 - 0 °C / Inert atmosphere

2.1: samarium diiodide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere; Schlenk technique

With samarium diiodide; sodium hydride; In tetrahydrofuran;

DOI:10.1002/ejoc.201300148

Reference yield:

(R)-5-((4S,5S)-2,2-dimethyl-5-(prop-1-en-2-yl)-1,3-dioxolan-4-yl)-2,2,3,3,8,8,9,9-octamethyl-4,7-dioxa-3,8-disiladecane (1453081-95-2) → (4R,5S)-3-((S)-3-((4R,5S)-2,2-dimethyl-5-(prop-1-en-2-yl)-1,3-dioxolan-4-yl)-3-hydroxy-2,2-dimethylpropanoyl)-5-methyl-4-phenyloxazolidin-2-one (1453081-98-5)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3.5 h / 0 - 20 °C / Inert atmosphere

2: water; sodium periodate / dichloromethane / 2 h / 0 °C

3: samarium diiodide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere; Schlenk technique

With sodium periodate; samarium diiodide; tetrabutyl ammonium fluoride; water; In tetrahydrofuran; dichloromethane;

DOI:10.1002/ejoc.201300148

upstream raw materials:

(4R,5S)-5-methyl-4-phenyloxazolidin-2-one

(4R,5S)-3-(2-bromo-2-methylpropanoyl)-5-methyl-4-phenyloxazolidin-2-one

(4S,5S)-2,2-dimethyl-5-(prop-1-en-2-yl)-1,3-dioxolane-4-carbaldehyde

2,2-dimethoxy-propane

Downstream raw materials:

(4R,5S)-3-((S)-3-((4R,5S)-2,2-dimethyl-5-(prop-1-en-2-yl)-1,3-dioxolan-4-yl)-3-(methoxymethoxy)-2,2-dimethylpropanoyl)-5-methyl-4-phenyloxazolidin-2-one