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

Base Information

Chemical Name:3-methyl-5-[1-methyl-2-(4-methylphenylsulfonyloxy)-(1R)-ethyl]-2-oxo-(4R,5R)-1,3-oxazolan-4-ylmethylacetate
CAS No.:689283-32-7
Molecular Formula:C₁₇H₂₃NO₇S
Molecular Weight:385.438
Hs Code.:

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

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

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

There total 4 articles about 3-methyl-5-[1-methyl-2-(4-methylphenylsulfonyloxy)-(1R)-ethyl]-2-oxo-(4R,5R)-1,3-oxazolan-4-ylmethylacetate 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: 85.0%

: 98-59-9
p-toluenesulfonyl chloride

: 689283-30-5
5-[2-hydroxy-1-methyl-(1R)-ethyl]-3-methyl-2-oxo-(4R,5R)-1,3-oxazolan-4-ylmethylacetate

: 689283-32-7
3-methyl-5-[1-methyl-2-(4-methylphenylsulfonyloxy)-(1R)-ethyl]-2-oxo-(4R,5R)-1,3-oxazolan-4-ylmethylacetate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1016/j.tet.2004.01.088

Reference yield:

: 628340-18-1
2-bromo-1-tert-butyldiphenylsilyloxy-4-methyl-5(RS_S)-phenylsulfinyl-(2R,3R,4S)-pentan-3-ol

: 689283-32-7
3-methyl-5-[1-methyl-2-(4-methylphenylsulfonyloxy)-(1R)-ethyl]-2-oxo-(4R,5R)-1,3-oxazolan-4-ylmethylacetate

Guidance literature:: Multi-step reaction with 8 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

6: Et₃N / acetonitrile / 0.5 h / 20 °C

7: 0.66 g / NaHCO₃; NaBH₄ / acetonitrile; H₂O / 0.5 h / 0 °C

8: 85 percent / DMAP; Et₃N / CH₂Cl₂ / 2 h / 20 °C

With dmap; sodium tetrahydroborate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; sodium hydrogencarbonate; potassium carbonate; acetic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; 6: Pummerer rearrangement;
DOI:10.1016/j.tet.2004.01.088

Reference yield:

: 689283-29-2
3-methyl-5-[1-methyl-2(RS_S)-phenylsulfinyl-(1S)-ethyl]-2-oxo-(4R,5R)-1,3-oxazolan-4-yl-methylacetate

: 689283-32-7
3-methyl-5-[1-methyl-2-(4-methylphenylsulfonyloxy)-(1R)-ethyl]-2-oxo-(4R,5R)-1,3-oxazolan-4-ylmethylacetate

Guidance literature:: Multi-step reaction with 3 steps

1: Et₃N / acetonitrile / 0.5 h / 20 °C

2: 0.66 g / NaHCO₃; NaBH₄ / acetonitrile; H₂O / 0.5 h / 0 °C

3: 85 percent / DMAP; Et₃N / CH₂Cl₂ / 2 h / 20 °C

With dmap; sodium tetrahydroborate; sodium hydrogencarbonate; triethylamine; In dichloromethane; water; acetonitrile; 1: Pummerer rearrangement;
DOI:10.1016/j.tet.2004.01.088