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

Base Information

• Chemical Name: 4-hydroxymethyl-3-methyl-5-[1-methyl-2(RS_S)-phenylsulfinyl-(1S)-ethyl]-(4R,5R)-1,3-oxazolan-2-one
• CAS No.: 689283-26-9
• Molecular Formula: C₁₄H₁₉NO₄S
• Molecular Weight: 297.375

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

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

Chemical Property:

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

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

2-N-methylcarbonyloxymethyl-3-[1-methyl-2(RSS)-phenylsulfinyl-(1S)-ethyl]-(2S,3R)-oxirane (689283-24-7) → 4-hydroxymethyl-3-methyl-5-[1-methyl-2(RSS)-phenylsulfinyl-(1S)-ethyl]-(4R,5R)-1,3-oxazolan-2-one (689283-26-9)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; 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) → 4-hydroxymethyl-3-methyl-5-[1-methyl-2(RSS)-phenylsulfinyl-(1S)-ethyl]-(4R,5R)-1,3-oxazolan-2-one (689283-26-9)

Guidance literature:

Multi-step reaction with 4 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

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) → 4-hydroxymethyl-3-methyl-5-[1-methyl-2(RSS)-phenylsulfinyl-(1S)-ethyl]-(4R,5R)-1,3-oxazolan-2-one (689283-26-9)

Guidance literature:

Multi-step reaction with 3 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

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

DOI:10.1016/j.tet.2004.01.088

upstream raw materials:

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

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

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