(4R,5S)-3-{(2S,4Z)-2-[3-(trimethylsilyl)prop-2-ynyl]hept-4-enoyl}-4-methyl-5-phenyloxazolidin-2-one

Base Information

• Chemical Name: (4R,5S)-3-{(2S,4Z)-2-[3-(trimethylsilyl)prop-2-ynyl]hept-4-enoyl}-4-methyl-5-phenyloxazolidin-2-one
• CAS No.: 948042-09-9
• Molecular Formula: C₂₃H₃₁NO₃Si
• Molecular Weight: 397.59

Synonyms:(4R,5S)-3-{(2S,4Z)-2-[3-(trimethylsilyl)prop-2-ynyl]hept-4-enoyl}-4-methyl-5-phenyloxazolidin-2-one

Chemical Property of (4R,5S)-3-{(2S,4Z)-2-[3-(trimethylsilyl)prop-2-ynyl]hept-4-enoyl}-4-methyl-5-phenyloxazolidin-2-one

Chemical Property:

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Technology Process of (4R,5S)-3-{(2S,4Z)-2-[3-(trimethylsilyl)prop-2-ynyl]hept-4-enoyl}-4-methyl-5-phenyloxazolidin-2-one

There total 3 articles about (4R,5S)-3-{(2S,4Z)-2-[3-(trimethylsilyl)prop-2-ynyl]hept-4-enoyl}-4-methyl-5-phenyloxazolidin-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: 65.0%

(4R,5S)-3-[(Z)-hept-4-enoyl]-4-methyl-5-phenyloxazolidin-2-one (948042-46-4) + 3-bromo-1-trimethylsilylprop-2-yne (102046-77-5) → (4R,5S)-3-{(2S,4Z)-2-[3-(trimethylsilyl)prop-2-ynyl]hept-4-enoyl}-4-methyl-5-phenyloxazolidin-2-one (948042-09-9) + C23H31NO3Si

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; toluene; at 0 ℃; for 3h;

DOI:10.1002/chem.200601685

Reference yield:

4-methyl-5-phenyloxazolidin-2-one (77943-39-6) → (4R,5S)-3-{(2S,4Z)-2-[3-(trimethylsilyl)prop-2-ynyl]hept-4-enoyl}-4-methyl-5-phenyloxazolidin-2-one (948042-09-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine; pivaloyl chloride / tetrahydrofuran / 1 h / 0 °C

1.2: 59 percent / DMAP; triethylamine / tetrahydrofuran / 12 h / 20 °C

2.1: 65 percent / LiHMDS / tetrahydrofuran; toluene / 3 h / 0 °C

With pivaloyl chloride; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; toluene;

DOI:10.1002/chem.200601685

Reference yield:

(Z)-4-heptenoic acid (41653-95-6) → (4R,5S)-3-{(2S,4Z)-2-[3-(trimethylsilyl)prop-2-ynyl]hept-4-enoyl}-4-methyl-5-phenyloxazolidin-2-one (948042-09-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine; pivaloyl chloride / tetrahydrofuran / 1 h / 0 °C

1.2: 59 percent / DMAP; triethylamine / tetrahydrofuran / 12 h / 20 °C

2.1: 65 percent / LiHMDS / tetrahydrofuran; toluene / 3 h / 0 °C

With pivaloyl chloride; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; toluene;

DOI:10.1002/chem.200601685

upstream raw materials:

(4R,5S)-3-[(Z)-hept-4-enoyl]-4-methyl-5-phenyloxazolidin-2-one

3-bromo-1-trimethylsilylprop-2-yne

4-methyl-5-phenyloxazolidin-2-one

(Z)-4-heptenoic acid

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