(2S,3R)-4-Benzyl-3-[3-hydroxy-2-methyl-1-oxo-3-[(4-phenylsulfanyl)-3,4,5,6-tetrahydro-(2H)-pyran-4-yl]propionyl]oxazolidin-2-one

Base Information

• Chemical Name: (2S,3R)-4-Benzyl-3-[3-hydroxy-2-methyl-1-oxo-3-[(4-phenylsulfanyl)-3,4,5,6-tetrahydro-(2H)-pyran-4-yl]propionyl]oxazolidin-2-one
• CAS No.: 179238-94-9
• Molecular Formula: C₂₅H₂₉NO₅S
• Molecular Weight: 455.575
• Mol file: 179238-94-9.mol

Synonyms:(2S,3R)-4-Benzyl-3-[3-hydroxy-2-methyl-1-oxo-3-[(4-phenylsulfanyl)-3,4,5,6-tetrahydro-(2H)-pyran-4-yl]propionyl]oxazolidin-2-one

Chemical Property of (2S,3R)-4-Benzyl-3-[3-hydroxy-2-methyl-1-oxo-3-[(4-phenylsulfanyl)-3,4,5,6-tetrahydro-(2H)-pyran-4-yl]propionyl]oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-4-Benzyl-3-[3-hydroxy-2-methyl-1-oxo-3-[(4-phenylsulfanyl)-3,4,5,6-tetrahydro-(2H)-pyran-4-yl]propionyl]oxazolidin-2-one

There total 5 articles about (2S,3R)-4-Benzyl-3-[3-hydroxy-2-methyl-1-oxo-3-[(4-phenylsulfanyl)-3,4,5,6-tetrahydro-(2H)-pyran-4-yl]propionyl]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: 94.0%

(S)-4-benzyl-3-propionyl-2-oxazolidinone (131685-53-5,101711-78-8) + 4-(Phenylsulfanyl)-3,4,5,6-tetrahydropyran-4(2H)-carboxaldehyde (179088-48-3) → (2S,3R)-4-Benzyl-3-[3-hydroxy-2-methyl-1-oxo-3-[(4-phenylsulfanyl)-3,4,5,6-tetrahydro-(2H)-pyran-4-yl]propionyl]oxazolidin-2-one (179238-94-9)

Guidance literature:

With di-n-butylboryl trifluoromethanesulfonate; diethylaluminium chloride; N-ethyl-N,N-diisopropylamine;

DOI:10.1016/0040-4039(96)00851-9

Reference yield:

di-n-butylboron enolate of (S)-4-benzyl-N-propionyl-2-oxazolidinone (211504-69-7) + 4-(Phenylsulfanyl)-3,4,5,6-tetrahydropyran-4(2H)-carboxaldehyde (179088-48-3) → (2S,3R)-4-Benzyl-3-[3-hydroxy-2-methyl-1-oxo-3-[(4-phenylsulfanyl)-3,4,5,6-tetrahydro-(2H)-pyran-4-yl]propionyl]oxazolidin-2-one (179238-94-9)

Guidance literature:

di-n-butylboron enolate of (S)-4-benzyl-N-propionyl-2-oxazolidinone; 4-(Phenylsulfanyl)-3,4,5,6-tetrahydropyran-4(2H)-carboxaldehyde; With diethylaluminium chloride; In hexane; dichloromethane; at -88 ℃; for 5h;

With dihydrogen peroxide; In methanol; hexane; dichloromethane; at -88 - 0 ℃; for 1h; Further stages.;

DOI:10.1039/b001893g

Reference yield:

methoxymethyl phenyl sulfide (13865-50-4) → (2S,3R)-4-Benzyl-3-[3-hydroxy-2-methyl-1-oxo-3-[(4-phenylsulfanyl)-3,4,5,6-tetrahydro-(2H)-pyran-4-yl]propionyl]oxazolidin-2-one (179238-94-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / -78 °C

1.2: 78 percent / hexane; tetrahydrofuran / 0.33 h / -78 °C

2.1: 74 percent / SOCl₂; Et₃N / CH₂Cl₂ / 0.75 h

3.1: Et₂AlCl / CH₂Cl₂; hexane / 5 h / -88 °C

3.2: 0.58 g / aq. H₂O₂ / CH₂Cl₂; methanol; hexane / 1 h / -88 - 0 °C

With n-butyllithium; thionyl chloride; diethylaluminium chloride; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 1.1: Metallation / 1.2: Addition / 2.1: Rearrangement / 3.1: Addition / 3.2: Oxidation;

DOI:10.1039/b001893g

upstream raw materials:

(S)-4-benzyl-3-propionyl-2-oxazolidinone

4-(Phenylsulfanyl)-3,4,5,6-tetrahydropyran-4(2H)-carboxaldehyde

di-n-butylboron enolate of (S)-4-benzyl-N-propionyl-2-oxazolidinone

methoxymethyl phenyl sulfide

Downstream raw materials:

(2S,3R)-2-Methyl-1-(4-phenylsulfanyl-3,4,5,6-tetrahydro-(2H)-pyran-4-yl)propane-1,3-diol