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

Base Information

• Chemical Name: (-)-(R)-4-benzyl-3-((2R,3S,4S)-3-hydroxy-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentanoyl)oxazolidin-2-one
• CAS No.: 303727-83-5
• Molecular Formula: C₂₅H₃₁NO₆
• Molecular Weight: 441.524
• Mol file: 303727-83-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about (-)-(R)-4-benzyl-3-((2R,3S,4S)-3-hydroxy-5-((4-methoxybenzyl)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: 89.0%

(2S)-3-[(4-methoxybenzyl)oxy]-2-methylpropanal (132969-60-9) + (3R)-3-propionyl-4-benzyloxazolidin-2-one (101711-78-8,131685-53-5) → (-)-(R)-4-benzyl-3-((2R,3S,4S)-3-hydroxy-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentanoyl)oxazolidin-2-one (303727-83-5)

Guidance literature:

(2S)-3-[(4-methoxybenzyl)oxy]-2-methylpropanal; (3R)-3-propionyl-4-benzyloxazolidin-2-one; With di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane; at -78 - 0 ℃; for 4h;

With dihydrogen peroxide; In methanol; at 20 ℃; Further stages.;

DOI:10.1021/ja0015287

Reference yield: 70.0%

di-n-butylboryl trifluoromethanesulfonate (60669-69-4) + (2S)-3-[(4-methoxybenzyl)oxy]-2-methylpropanal (132969-60-9) + (3R)-3-propionyl-4-benzyloxazolidin-2-one (101711-78-8,131685-53-5) → (-)-(R)-4-benzyl-3-((2R,3S,4S)-3-hydroxy-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentanoyl)oxazolidin-2-one (303727-83-5)

Guidance literature:

di-n-butylboryl trifluoromethanesulfonate; (3R)-3-propionyl-4-benzyloxazolidin-2-one; In dichloromethane; at -10 ℃; Inert atmosphere;

(2S)-3-[(4-methoxybenzyl)oxy]-2-methylpropanal; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 - -10 ℃; for 2.5h; diastereoselective reaction; Inert atmosphere;

DOI:10.1002/anie.201500401

Reference yield: 36.0%

(+)-(S)-3-(4-methoxybenzyloxy)-2-methylpropionaldehyde + (3R)-3-propionyl-4-benzyloxazolidin-2-one (101711-78-8,131685-53-5) → (-)-(R)-4-benzyl-3-((2R,3S,4S)-3-hydroxy-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentanoyl)oxazolidin-2-one (303727-83-5)

Guidance literature:

(3R)-3-propionyl-4-benzyloxazolidin-2-one; With di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane; at 0 ℃; for 0.916667h; Inert atmosphere;

(+)-(S)-3-(4-methoxybenzyloxy)-2-methylpropionaldehyde; In dichloromethane; at -78 - 20 ℃; for 15h; Inert atmosphere;

DOI:10.1002/chem.201406252

upstream raw materials:

(2S)-3-[(4-methoxybenzyl)oxy]-2-methylpropanal

(3R)-3-propionyl-4-benzyloxazolidin-2-one

O-(4-methoxybenzyl)-trichloroacetimidate

methyl (2S)-[(4-methoxybenzyl)oxy]-2-methylpropanoate

Downstream raw materials:

(2R,3S,4S)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylpentanoic acid methoxymethylamide

C₂₅H₂₉NO₆

(-)-(2S,3R,4S)-3-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentan-1-ol

ethyl (4S,5R,6S,2E)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-4,6-dimethylhept-2-enoate