[(5E,7E,10E)-(2S,13S,14R)-13-Hydroxy-2,8,10,14-tetramethyl-15-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-15-oxo-pentadeca-5,7,10-trienyl]-(4-methoxy-benzyl)-carbamic acid 2-trimethylsilanyl-ethyl ester

Base Information

• Chemical Name: [(5E,7E,10E)-(2S,13S,14R)-13-Hydroxy-2,8,10,14-tetramethyl-15-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-15-oxo-pentadeca-5,7,10-trienyl]-(4-methoxy-benzyl)-carbamic acid 2-trimethylsilanyl-ethyl ester
• CAS No.: 213194-72-0
• Molecular Formula: C₄₃H₆₂N₂O₇Si
• Molecular Weight: 747.06

Synonyms:

Chemical Property of [(5E,7E,10E)-(2S,13S,14R)-13-Hydroxy-2,8,10,14-tetramethyl-15-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-15-oxo-pentadeca-5,7,10-trienyl]-(4-methoxy-benzyl)-carbamic acid 2-trimethylsilanyl-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of [(5E,7E,10E)-(2S,13S,14R)-13-Hydroxy-2,8,10,14-tetramethyl-15-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-15-oxo-pentadeca-5,7,10-trienyl]-(4-methoxy-benzyl)-carbamic acid 2-trimethylsilanyl-ethyl ester

There total 17 articles about [(5E,7E,10E)-(2S,13S,14R)-13-Hydroxy-2,8,10,14-tetramethyl-15-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-15-oxo-pentadeca-5,7,10-trienyl]-(4-methoxy-benzyl)-carbamic acid 2-trimethylsilanyl-ethyl ester 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: 58.0%

(4R,5S)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one (77877-20-4) + (4-Methoxy-benzyl)-((5E,7E,10E)-(S)-2,8,10-trimethyl-13-oxo-trideca-5,7,10-trienyl)-carbamic acid 2-trimethylsilanyl-ethyl ester (213195-33-6) → [(5E,7E,10E)-(2S,13S,14R)-13-Hydroxy-2,8,10,14-tetramethyl-15-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-15-oxo-pentadeca-5,7,10-trienyl]-(4-methoxy-benzyl)-carbamic acid 2-trimethylsilanyl-ethyl ester (213194-72-0)

Guidance literature:

With di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane;

DOI:10.7164/antibiotics.51.688

Reference yield:

(E)-4-methylhept-3-en-6-yn-1-ol (13857-47-1) → [(5E,7E,10E)-(2S,13S,14R)-13-Hydroxy-2,8,10,14-tetramethyl-15-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-15-oxo-pentadeca-5,7,10-trienyl]-(4-methoxy-benzyl)-carbamic acid 2-trimethylsilanyl-ethyl ester (213194-72-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 99 percent / dimethylformamide

2.1: 88 percent / I₂ / Cp₂ZrCl₂ / CH₂Cl₂

3.1: 99 percent / TBAF / tetrahydrofuran

4.1: tetrahydrofuran

4.2: 52 percent / NaOEt / Pd(PPh₃)4 / ethanol; benzene / Heating

5.1: Dess-Martin reagent / CH₂Cl₂

6.1: 58 percent / Buⁿ2BOTf; Et₃N / CH₂Cl₂

With di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; iodine; Dess-Martin periodane; triethylamine; zirconocene dichloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1.1: Etherification / 2.1: Addition / 3.1: Hydrolysis / 4.1: Addition / 4.2: Addition / 5.1: Dess-Martin oxidation / 6.1: Evans aldol reaction;

DOI:10.7164/antibiotics.51.688

Reference yield:

(E)-7-acetoxy-4-methylhept-4-en-1-yne (13927-59-8) → [(5E,7E,10E)-(2S,13S,14R)-13-Hydroxy-2,8,10,14-tetramethyl-15-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-15-oxo-pentadeca-5,7,10-trienyl]-(4-methoxy-benzyl)-carbamic acid 2-trimethylsilanyl-ethyl ester (213194-72-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 98 percent / KCN / ethanol

2.1: 99 percent / dimethylformamide

3.1: 88 percent / I₂ / Cp₂ZrCl₂ / CH₂Cl₂

4.1: 99 percent / TBAF / tetrahydrofuran

5.1: tetrahydrofuran

5.2: 52 percent / NaOEt / Pd(PPh₃)4 / ethanol; benzene / Heating

6.1: Dess-Martin reagent / CH₂Cl₂

7.1: 58 percent / Buⁿ2BOTf; Et₃N / CH₂Cl₂

With potassium cyanide; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; iodine; Dess-Martin periodane; triethylamine; zirconocene dichloride; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Deacetylation / 2.1: Etherification / 3.1: Addition / 4.1: Hydrolysis / 5.1: Addition / 5.2: Addition / 6.1: Dess-Martin oxidation / 7.1: Evans aldol reaction;

DOI:10.7164/antibiotics.51.688

upstream raw materials:

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

(4-Methoxy-benzyl)-((5E,7E,10E)-(S)-2,8,10-trimethyl-13-oxo-trideca-5,7,10-trienyl)-carbamic acid 2-trimethylsilanyl-ethyl ester

(S)-3,7-dimethyl-6-octen-1-ol

(E)-4-methylhept-3-en-6-yn-1-ol

Downstream raw materials:

[(5E,7E,10E)-(2S,13S,14R)-13-(1-Ethoxy-ethoxy)-2,8,10,14-tetramethyl-15-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-15-oxo-pentadeca-5,7,10-trienyl]-(4-methoxy-benzyl)-carbamic acid 2-trimethylsilanyl-ethyl ester

(3E,5E,10E,13E,15E)-(7S,8S,19S)-8-(1-Ethoxy-ethoxy)-1-(4-methoxy-benzyl)-7,11,13,19-tetramethyl-azacycloicosa-3,5,10,13,15-pentaen-2-one

(2E,4E,9E,12E,14E)-(6S,7S,18S)-7-(1-Ethoxy-ethoxy)-19-(4-methoxy-benzylamino)-6,10,12,18-tetramethyl-nonadeca-2,4,9,12,14-pentaenoic acid

[(5E,7E,10E)-(2S,13S,14R)-13-(1-Ethoxy-ethoxy)-2,8,10,14-tetramethyl-15-oxo-pentadeca-5,7,10-trienyl]-(4-methoxy-benzyl)-carbamic acid 2-trimethylsilanyl-ethyl ester

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