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

Base Information

• Chemical Name: 2-tert-butyldiphenylsilyloxymethyl-3-[1-methyl-2(RS_S)-phenylsulfinyl-(1S)-ethyl]-(2S,3R)-oxirane
• CAS No.: 689283-22-5
• Molecular Formula: C₂₈H₃₄O₃SSi
• Molecular Weight: 478.728

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

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

Chemical Property:

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

There total 1 articles about 2-tert-butyldiphenylsilyloxymethyl-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-tert-butyldiphenylsilyloxy-4-methyl-5(RSS)-phenylsulfinyl-(2R,3R,4S)-pentan-3-ol (628340-18-1) → 2-tert-butyldiphenylsilyloxymethyl-3-[1-methyl-2(RSS)-phenylsulfinyl-(1S)-ethyl]-(2S,3R)-oxirane (689283-22-5)

Guidance literature:

With potassium carbonate; In methanol; at 0 - 20 ℃;

DOI:10.1016/j.tet.2004.01.088

Reference yield: 90.0%

2-tert-butyldiphenylsilyloxymethyl-3-[1-methyl-2(RSS)-phenylsulfinyl-(1S)-ethyl]-(2S,3R)-oxirane (689283-22-5) → 3-[1-methyl-2(RSS)-phenylsulfinyl-(1S)-ethyl]-(2S,3R)-oxiran-2-ylmethanol (689283-23-6)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 0 ℃; for 2h;

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

Guidance literature:

Multi-step reaction with 2 steps

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

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

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

DOI:10.1016/j.tet.2004.01.088

upstream raw materials:

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

Downstream raw materials:

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

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

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

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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