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

Base Information

• Chemical Name: 2-N-methylcarbonyloxymethyl-3-[1-methyl-2(RS_S)-phenylsulfinyl-(1S)-ethyl]-(2S,3R)-oxirane
• CAS No.: 689283-24-7
• Molecular Formula: C₁₄H₁₉NO₄S
• Molecular Weight: 297.375
• Mol file: 689283-24-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about 2-N-methylcarbonyloxymethyl-3-[1-methyl-2(RS_S)-phenylsulfinyl-(1S)-ethyl]-(2S,3R)-oxirane 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-bromo-1-N-methylcarbonyloxy-4-methyl-5(RSS)-phenylsulfinyl-(2R,3R,4S)-pentan-3-ol (689283-28-1) → 2-N-methylcarbonyloxymethyl-3-[1-methyl-2(RSS)-phenylsulfinyl-(1S)-ethyl]-(2S,3R)-oxirane (689283-24-7)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 1h;

DOI:10.1016/j.tet.2004.01.088

Reference yield: 90.0%

methyl isocyanate (624-83-9) + 3-[1-methyl-2(RSS)-phenylsulfinyl-(1S)-ethyl]-(2S,3R)-oxiran-2-ylmethanol (689283-23-6) → 2-N-methylcarbonyloxymethyl-3-[1-methyl-2(RSS)-phenylsulfinyl-(1S)-ethyl]-(2S,3R)-oxirane (689283-24-7)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 2h;

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) → 2-N-methylcarbonyloxymethyl-3-[1-methyl-2(RSS)-phenylsulfinyl-(1S)-ethyl]-(2S,3R)-oxirane (689283-24-7)

Guidance literature:

Multi-step reaction with 3 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

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

DOI:10.1016/j.tet.2004.01.088

upstream raw materials:

methyl isocyanate

3-[1-methyl-2(RS_S)-phenylsulfinyl-(1S)-ethyl]-(2S,3R)-oxiran-2-ylmethanol

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

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

Downstream raw materials:

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