(4R,5S)-3-[(2R,3S,7S)-3-Hydroxy-7-(4-methoxy-benzyloxy)-2,8-dimethyl-nonanoyl]-4-methyl-5-phenyl-oxazolidin-2-one

Base Information

• Chemical Name: (4R,5S)-3-[(2R,3S,7S)-3-Hydroxy-7-(4-methoxy-benzyloxy)-2,8-dimethyl-nonanoyl]-4-methyl-5-phenyl-oxazolidin-2-one
• CAS No.: 184104-23-2
• Molecular Formula: C₂₉H₃₉NO₆
• Molecular Weight: 497.632

Synonyms:(4R,5S)-3-[(2R,3S,7S)-3-Hydroxy-7-(4-methoxy-benzyloxy)-2,8-dimethyl-nonanoyl]-4-methyl-5-phenyl-oxazolidin-2-one

Chemical Property of (4R,5S)-3-[(2R,3S,7S)-3-Hydroxy-7-(4-methoxy-benzyloxy)-2,8-dimethyl-nonanoyl]-4-methyl-5-phenyl-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S)-3-[(2R,3S,7S)-3-Hydroxy-7-(4-methoxy-benzyloxy)-2,8-dimethyl-nonanoyl]-4-methyl-5-phenyl-oxazolidin-2-one

There total 8 articles about (4R,5S)-3-[(2R,3S,7S)-3-Hydroxy-7-(4-methoxy-benzyloxy)-2,8-dimethyl-nonanoyl]-4-methyl-5-phenyl-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: 98.0%

(4R,5S)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one (77877-20-4) + (S)-5-(4-Methoxy-benzyloxy)-6-methyl-heptanal (184104-22-1) → (4R,5S)-3-[(2R,3S,7S)-3-Hydroxy-7-(4-methoxy-benzyloxy)-2,8-dimethyl-nonanoyl]-4-methyl-5-phenyl-oxazolidin-2-one (184104-23-2)

Guidance literature:

With di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane; at -78 ℃;

DOI:10.1016/0040-4039(96)01653-X

Reference yield:

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) → (4R,5S)-3-[(2R,3S,7S)-3-Hydroxy-7-(4-methoxy-benzyloxy)-2,8-dimethyl-nonanoyl]-4-methyl-5-phenyl-oxazolidin-2-one (184104-23-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 58 percent / TfOH / diethyl ether / 23 °C

2: 98 percent / LiAlH₄ / tetrahydrofuran / 0 °C

3: 98 percent / pyridine / 0 °C

4: CuI / diethyl ether / 95 h / 0 °C

5: 1.) 9-BBN; 2.) 30percent H₂O₂, NaOH / 1.) THF, 23 deg C; 2.) THF, H₂O, 23 deg C

6: 94 percent / DMSO, (COCl)2, Et₃N / CH₂Cl₂ / -78 deg C -> 0 deg C

7: 98 percent / Bu₂BOTf, Et₃N / CH₂Cl₂ / -78 °C

With sodium hydroxide; copper(l) iodide; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane;

DOI:10.1016/0040-4039(96)01653-X

Reference yield:

(R)-methyl 2-hydroxy-3-methylbutanoate (90244-32-9) → (4R,5S)-3-[(2R,3S,7S)-3-Hydroxy-7-(4-methoxy-benzyloxy)-2,8-dimethyl-nonanoyl]-4-methyl-5-phenyl-oxazolidin-2-one (184104-23-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 58 percent / TfOH / diethyl ether / 23 °C

2: 98 percent / LiAlH₄ / tetrahydrofuran / 0 °C

3: 98 percent / pyridine / 0 °C

4: CuI / diethyl ether / 95 h / 0 °C

5: 1.) 9-BBN; 2.) 30percent H₂O₂, NaOH / 1.) THF, 23 deg C; 2.) THF, H₂O, 23 deg C

6: 94 percent / DMSO, (COCl)2, Et₃N / CH₂Cl₂ / -78 deg C -> 0 deg C

7: 98 percent / Bu₂BOTf, Et₃N / CH₂Cl₂ / -78 °C

With sodium hydroxide; copper(l) iodide; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane;

DOI:10.1016/0040-4039(96)01653-X

upstream raw materials:

(4R,5S)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one

(S)-5-(4-Methoxy-benzyloxy)-6-methyl-heptanal

O-(4-methoxybenzyl)-trichloroacetimidate

(R)-methyl 2-hydroxy-3-methylbutanoate

Downstream raw materials:

4-Nitro-benzoic acid (1R,5S)-5-(4-methoxy-benzyloxy)-6-methyl-1-[(R)-1-methyl-2-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-2-oxo-ethyl]-heptyl ester

(E)-(7S,8R)-8-[(2R,3R,7S)-3-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,8-dimethyl-nonanoyloxy]-4,7-dimethyl-3-oxo-non-4-enoic acid tert-butyl ester

(2R,3R,7S)-3-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,8-dimethyl-nonanoic acid

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