(S)-4-Benzyl-3-[(Z)-(S)-5-methyl-6-(tetrahydro-pyran-2-yloxy)-2-triethylsilanyloxy-hex-4-enoyl]-oxazolidin-2-one

Base Information

• Chemical Name: (S)-4-Benzyl-3-[(Z)-(S)-5-methyl-6-(tetrahydro-pyran-2-yloxy)-2-triethylsilanyloxy-hex-4-enoyl]-oxazolidin-2-one
• CAS No.: 350493-55-9
• Molecular Formula: C₂₈H₄₃NO₆Si
• Molecular Weight: 517.738

Synonyms:(S)-4-Benzyl-3-[(Z)-(S)-5-methyl-6-(tetrahydro-pyran-2-yloxy)-2-triethylsilanyloxy-hex-4-enoyl]-oxazolidin-2-one

Chemical Property of (S)-4-Benzyl-3-[(Z)-(S)-5-methyl-6-(tetrahydro-pyran-2-yloxy)-2-triethylsilanyloxy-hex-4-enoyl]-oxazolidin-2-one

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Technology Process of (S)-4-Benzyl-3-[(Z)-(S)-5-methyl-6-(tetrahydro-pyran-2-yloxy)-2-triethylsilanyloxy-hex-4-enoyl]-oxazolidin-2-one

There total 4 articles about (S)-4-Benzyl-3-[(Z)-(S)-5-methyl-6-(tetrahydro-pyran-2-yloxy)-2-triethylsilanyloxy-hex-4-enoyl]-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: 78.0%

triethylsilyl trifluoromethyl sulfonate (79271-56-0) + (S)-4-Benzyl-3-[(Z)-(S)-2-hydroxy-5-methyl-6-(tetrahydro-pyran-2-yloxy)-hex-4-enoyl]-oxazolidin-2-one (220889-34-9) → (S)-4-Benzyl-3-[(Z)-(S)-5-methyl-6-(tetrahydro-pyran-2-yloxy)-2-triethylsilanyloxy-hex-4-enoyl]-oxazolidin-2-one (350493-55-9)

Guidance literature:

(S)-4-Benzyl-3-[(Z)-(S)-2-hydroxy-5-methyl-6-(tetrahydro-pyran-2-yloxy)-hex-4-enoyl]-oxazolidin-2-one; With 2,6-dimethylpyridine; In dichloromethane; for 0.0666667h;

triethylsilyl trifluoromethyl sulfonate; In dichloromethane; at -78 ℃; for 0.5h; Further stages.;

DOI:10.1021/ja010454b

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) → (S)-4-Benzyl-3-[(Z)-(S)-5-methyl-6-(tetrahydro-pyran-2-yloxy)-2-triethylsilanyloxy-hex-4-enoyl]-oxazolidin-2-one (350493-55-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 96 percent / PPTS / CH₂Cl₂ / 1.5 h

2.1: t-BuLi / tetrahydrofuran; diethyl ether; pentane / 0.33 h / -78 °C

2.2: CuCN / tetrahydrofuran; diethyl ether; pentane / 1.08 h / -78 - -40 °C

2.3: 89 percent / tetrahydrofuran; diethyl ether; pentane / -78 - 0 °C

3.1: NaHMDS / tetrahydrofuran / 0.83 h / -78 °C

3.2: Davis' oxaziridine / tetrahydrofuran / 0.1 h

3.3: 71 percent / CSA / tetrahydrofuran / 0.03 h

4.1: 2,6-lutidine / CH₂Cl₂ / 0.07 h

4.2: 78 percent / CH₂Cl₂ / 0.5 h / -78 °C

With 2,6-dimethylpyridine; tert.-butyl lithium; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; In tetrahydrofuran; diethyl ether; dichloromethane; pentane;

DOI:10.1021/ja010454b

Reference yield:

(Z)-1-iodo-2-methyl-3-(2-tetrahydropyranyloxy)-1-propene (84039-75-8) → (S)-4-Benzyl-3-[(Z)-(S)-5-methyl-6-(tetrahydro-pyran-2-yloxy)-2-triethylsilanyloxy-hex-4-enoyl]-oxazolidin-2-one (350493-55-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: t-BuLi / tetrahydrofuran; diethyl ether; pentane / 0.33 h / -78 °C

1.2: CuCN / tetrahydrofuran; diethyl ether; pentane / 1.08 h / -78 - -40 °C

1.3: 89 percent / tetrahydrofuran; diethyl ether; pentane / -78 - 0 °C

2.1: NaHMDS / tetrahydrofuran / 0.83 h / -78 °C

2.2: Davis' oxaziridine / tetrahydrofuran / 0.1 h

2.3: 71 percent / CSA / tetrahydrofuran / 0.03 h

3.1: 2,6-lutidine / CH₂Cl₂ / 0.07 h

3.2: 78 percent / CH₂Cl₂ / 0.5 h / -78 °C

With 2,6-dimethylpyridine; tert.-butyl lithium; sodium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; pentane;

DOI:10.1021/ja010454b

upstream raw materials:

triethylsilyl trifluoromethyl sulfonate

(S)-4-Benzyl-3-[(Z)-(S)-2-hydroxy-5-methyl-6-(tetrahydro-pyran-2-yloxy)-hex-4-enoyl]-oxazolidin-2-one

3,4-dihydro-2H-pyran

(Z)-1-iodo-2-methyl-3-(2-tetrahydropyranyloxy)-1-propene

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