(S)-4-benzyl-3-{(2S,3R,4R)-3-hydroxy-5-[(4methoxybenzyl)oxy]-2,4-dimethylpentanoyl}oxazolidin-2-one

Base Information

• Chemical Name: (S)-4-benzyl-3-{(2S,3R,4R)-3-hydroxy-5-[(4methoxybenzyl)oxy]-2,4-dimethylpentanoyl}oxazolidin-2-one
• CAS No.: 172269-36-2
• Molecular Formula: C₂₅H₃₁NO₆
• Molecular Weight: 441.524
• Mol file: 172269-36-2.mol

Synonyms:(S)-4-benzyl-3-{(2S,3R,4R)-3-hydroxy-5-[(4methoxybenzyl)oxy]-2,4-dimethylpentanoyl}oxazolidin-2-one

Chemical Property of (S)-4-benzyl-3-{(2S,3R,4R)-3-hydroxy-5-[(4methoxybenzyl)oxy]-2,4-dimethylpentanoyl}oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-benzyl-3-{(2S,3R,4R)-3-hydroxy-5-[(4methoxybenzyl)oxy]-2,4-dimethylpentanoyl}oxazolidin-2-one

There total 4 articles about (S)-4-benzyl-3-{(2S,3R,4R)-3-hydroxy-5-[(4methoxybenzyl)oxy]-2,4-dimethylpentanoyl}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: 75.0%

(S)-4-benzyl-3-propionyl-2-oxazolidinone (131685-53-5,101711-78-8) + (2R)-3-(4-methoxybenzyloxy)-2-methyl-1-propanal (160238-46-0) → (S)-4-benzyl-3-{(2S,3R,4R)-3-hydroxy-5-[(4methoxybenzyl)oxy]-2,4-dimethylpentanoyl}oxazolidin-2-one (172269-36-2)

Guidance literature:

(S)-4-benzyl-3-propionyl-2-oxazolidinone; With di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane; at 0 ℃; for 0.666667h;

(2R)-3-(4-methoxybenzyloxy)-2-methyl-1-propanal; In dichloromethane; at -78 - 0 ℃; for 4.25h; Further stages.;

DOI:10.1002/anie.200704893

Reference yield:

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) → (S)-4-benzyl-3-{(2S,3R,4R)-3-hydroxy-5-[(4methoxybenzyl)oxy]-2,4-dimethylpentanoyl}oxazolidin-2-one (172269-36-2)

Guidance literature:

Multi-step reaction with 4 steps

1: PPTS / CH₂Cl₂; cyclohexane

2: LiAlH₄ / tetrahydrofuran

3: (COCl)2, DMSO

4: n-Bu₂BOTf, Et₃N / CH₂Cl₂

With lithium aluminium tetrahydride; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; cyclohexane;

DOI:10.1021/ja00153a030

Reference yield:

(2S)-3-(4-methoxybenzyloxy)-2-methyl-1-propanol (160238-45-9) → (S)-4-benzyl-3-{(2S,3R,4R)-3-hydroxy-5-[(4methoxybenzyl)oxy]-2,4-dimethylpentanoyl}oxazolidin-2-one (172269-36-2)

Guidance literature:

Multi-step reaction with 2 steps

1: (COCl)2, DMSO

2: n-Bu₂BOTf, Et₃N / CH₂Cl₂

With oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; dimethyl sulfoxide; triethylamine; In dichloromethane;

DOI:10.1021/ja00153a030

upstream raw materials:

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

(2R)-3-(4-methoxybenzyloxy)-2-methyl-1-propanal

O-(4-methoxybenzyl)-trichloroacetimidate

(2S)-3-(4-methoxybenzyloxy)-2-methyl-1-propanol

Downstream raw materials:

(2S,3R,4R)-3-Hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-pentanoic acid methoxy-methyl-amide

(S)-3-((2S,3R,4R)-5-(4-methoxybenzyloxy)-3-((3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)diisopropylsilyloxy)-2,4-dimethylpentanoyl)-4-benzyloxazolidin-2-one

(1S,3R,4R,5S)-3-((R)-1-{(4R,5R,6S)-6-[(S)-1-(benzyloxy)propano-2-yl]-2,2,5-trimethyl-1,3-dioxan-4-yl}ethyl)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octane

C₆₄H₁₁₈O₈Si₄