(2'R,3'S,5'S,4R,5S)-3-(3'-Hydroxy-5',6'-(isopropylidenedioxy)-2'-(methylthio)hexanoyl)-4-methyl-5-phenyl-2-oxazolidinone

Base Information

• Chemical Name: (2'R,3'S,5'S,4R,5S)-3-(3'-Hydroxy-5',6'-(isopropylidenedioxy)-2'-(methylthio)hexanoyl)-4-methyl-5-phenyl-2-oxazolidinone
• CAS No.: 139631-10-0
• Molecular Formula: C₂₀H₂₇NO₆S
• Molecular Weight: 409.503
• Mol file: 139631-10-0.mol

Synonyms:(2'R,3'S,5'S,4R,5S)-3-(3'-Hydroxy-5',6'-(isopropylidenedioxy)-2'-(methylthio)hexanoyl)-4-methyl-5-phenyl-2-oxazolidinone

Chemical Property of (2'R,3'S,5'S,4R,5S)-3-(3'-Hydroxy-5',6'-(isopropylidenedioxy)-2'-(methylthio)hexanoyl)-4-methyl-5-phenyl-2-oxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2'R,3'S,5'S,4R,5S)-3-(3'-Hydroxy-5',6'-(isopropylidenedioxy)-2'-(methylthio)hexanoyl)-4-methyl-5-phenyl-2-oxazolidinone

There total 1 articles about (2'R,3'S,5'S,4R,5S)-3-(3'-Hydroxy-5',6'-(isopropylidenedioxy)-2'-(methylthio)hexanoyl)-4-methyl-5-phenyl-2-oxazolidinone 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:

2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde (32233-44-6) + (4R,5S)-3-(1'-oxo-2'-methylthioethyl)-4-methyl-5-phenyl-2-oxazolidinone (116857-38-6) → (2'R,3'S,5'S,4R,5S)-3-(3'-Hydroxy-5',6'-(isopropylidenedioxy)-2'-(methylthio)hexanoyl)-4-methyl-5-phenyl-2-oxazolidinone (139631-10-0)

Guidance literature:

With di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; Yield given. Multistep reaction; 1.) CH₂Cl₂, -7 to 0 deg C, 70 min, 2.) -78 to 23 deg C, 14 h;

DOI:10.1021/jo00034a010

Reference yield: 94.0%

(2'R,3'S,5'S,4R,5S)-3-(3'-Hydroxy-5',6'-(isopropylidenedioxy)-2'-(methylthio)hexanoyl)-4-methyl-5-phenyl-2-oxazolidinone (139631-10-0) → (3'S,5'S,4R,5S)-3-(3'-Hydroxy-5',6'-(isopropylidenedioxy)hexanoyl)-4-methyl-5-phenyl-2-oxazolidinone (139631-11-1)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; at 80 ℃; for 0.666667h;

DOI:10.1021/jo00034a010

Reference yield:

(2'R,3'S,5'S,4R,5S)-3-(3'-Hydroxy-5',6'-(isopropylidenedioxy)-2'-(methylthio)hexanoyl)-4-methyl-5-phenyl-2-oxazolidinone (139631-10-0) → Ethyl (2S,3S,5S)-3-((tert-butyldiphenylsilyl)oxy)-5,6-(isopropylidenedioxy)-2-methylhexanoate (139631-14-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / tributyltin hydride, AIBN / benzene / 0.67 h / 80 °C

2: 72 percent / tetrahydrofuran; ethanol / 1.17 h / 0 °C

3: 1.) lithium diisopropylamide, 2.) HMPA / 1.) THF, -55 to -30 deg C, 2 h, then to -20 deg C, 1 h, 2.) -78 to -55 deg C, 35 h

4: 87 percent / imidazole, DMAP / CH₂Cl₂ / 40 h / 40 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; lithium diisopropyl amide; In tetrahydrofuran; ethanol; dichloromethane; benzene;

DOI:10.1021/jo00034a010

upstream raw materials:

2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde

(4R,5S)-3-(1'-oxo-2'-methylthioethyl)-4-methyl-5-phenyl-2-oxazolidinone

Downstream raw materials:

(3'S,5'S,4R,5S)-3-(3'-Hydroxy-5',6'-(isopropylidenedioxy)hexanoyl)-4-methyl-5-phenyl-2-oxazolidinone

Ethyl (2S,3S,5S)-3-((tert-butyldiphenylsilyl)oxy)-5,6-(isopropylidenedioxy)-2-methylhexanoate

(3S,4S,6E,8E,10E)-3-((tert-Butyldiphenylsilyl)oxy)-4,6,10-trimethyl-11-(2'-methyloxazol-4'-yl)-1-oxo-6,8,10-undecatrien-5-one

(3S,4S,5S,6E,8E,10E)-3-((tert-Butyldiphenylsilyl)oxy)-5-hydroxy-4,6,10-trimethyl-11-(2'-methyloxazol-4'-yl)-6,8,10-undecatrienoic acid 1,5-lactone