3-methyl-5-[1-methyl-2(RS_S)-phenylsulfinyl-(1S)-ethyl]-2-oxo-(4R,5R)-1,3-oxazolan-4-yl-methylacetate

Base Information

• Chemical Name: 3-methyl-5-[1-methyl-2(RS_S)-phenylsulfinyl-(1S)-ethyl]-2-oxo-(4R,5R)-1,3-oxazolan-4-yl-methylacetate
• CAS No.: 689283-29-2
• Molecular Formula: C₁₆H₂₁NO₅S
• Molecular Weight: 339.412

Synonyms:3-methyl-5-[1-methyl-2(RS_S)-phenylsulfinyl-(1S)-ethyl]-2-oxo-(4R,5R)-1,3-oxazolan-4-yl-methylacetate

Chemical Property of 3-methyl-5-[1-methyl-2(RS_S)-phenylsulfinyl-(1S)-ethyl]-2-oxo-(4R,5R)-1,3-oxazolan-4-yl-methylacetate

Chemical Property:

Purity/Quality:

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Technology Process of 3-methyl-5-[1-methyl-2(RS_S)-phenylsulfinyl-(1S)-ethyl]-2-oxo-(4R,5R)-1,3-oxazolan-4-yl-methylacetate

There total 3 articles about 3-methyl-5-[1-methyl-2(RS_S)-phenylsulfinyl-(1S)-ethyl]-2-oxo-(4R,5R)-1,3-oxazolan-4-yl-methylacetate 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: 95.0%

acetic anhydride (108-24-7) + 4-hydroxymethyl-3-methyl-5-[1-methyl-2(RSS)-phenylsulfinyl-(1S)-ethyl]-(4R,5R)-1,3-oxazolan-2-one (689283-26-9) → 3-methyl-5-[1-methyl-2(RSS)-phenylsulfinyl-(1S)-ethyl]-2-oxo-(4R,5R)-1,3-oxazolan-4-yl-methylacetate (689283-29-2)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1016/j.tet.2004.01.088

Reference yield:

2-bromo-1-tert-butyldiphenylsilyloxy-4-methyl-5(RSS)-phenylsulfinyl-(2R,3R,4S)-pentan-3-ol (628340-18-1) → 3-methyl-5-[1-methyl-2(RSS)-phenylsulfinyl-(1S)-ethyl]-2-oxo-(4R,5R)-1,3-oxazolan-4-yl-methylacetate (689283-29-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / K₂CO₃ / methanol / 0 - 20 °C

2: 90 percent / acetic acid; tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 0 °C

3: 90 percent / Et₃N / CH₂Cl₂ / 2 h / 20 °C

4: 95 percent / NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

5: 95 percent / Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

With tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; potassium carbonate; acetic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/j.tet.2004.01.088

Reference yield:

2-tert-butyldiphenylsilyloxymethyl-3-[1-methyl-2(RSS)-phenylsulfinyl-(1S)-ethyl]-(2S,3R)-oxirane (689283-22-5) → 3-methyl-5-[1-methyl-2(RSS)-phenylsulfinyl-(1S)-ethyl]-2-oxo-(4R,5R)-1,3-oxazolan-4-yl-methylacetate (689283-29-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / acetic acid; tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 0 °C

2: 90 percent / Et₃N / CH₂Cl₂ / 2 h / 20 °C

3: 95 percent / NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

4: 95 percent / Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

With tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2004.01.088

upstream raw materials:

acetic anhydride

4-hydroxymethyl-3-methyl-5-[1-methyl-2(RS_S)-phenylsulfinyl-(1S)-ethyl]-(4R,5R)-1,3-oxazolan-2-one

2-bromo-1-tert-butyldiphenylsilyloxy-4-methyl-5(RS_S)-phenylsulfinyl-(2R,3R,4S)-pentan-3-ol

2-tert-butyldiphenylsilyloxymethyl-3-[1-methyl-2(RS_S)-phenylsulfinyl-(1S)-ethyl]-(2S,3R)-oxirane

Downstream raw materials:

3-methyl-5-[1-methyl-2-(4-methylphenylsulfonyloxy)-(1R)-ethyl]-2-oxo-(4R,5R)-1,3-oxazolan-4-ylmethylacetate

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