2-tert-butyldimethylsilyloxy-2-[3-methyl-2-oxo-5-phenyl-(4S,5R)-1,4-oxazolan-4-yl]-acetaldehyde

Base Information

Chemical Name:2-tert-butyldimethylsilyloxy-2-[3-methyl-2-oxo-5-phenyl-(4S,5R)-1,4-oxazolan-4-yl]-acetaldehyde
CAS No.:651359-04-5
Molecular Formula:C₁₈H₂₇NO₄Si
Molecular Weight:349.502
Hs Code.:

Synonyms:2-tert-butyldimethylsilyloxy-2-[3-methyl-2-oxo-5-phenyl-(4S,5R)-1,4-oxazolan-4-yl]-acetaldehyde

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Chemical Property of 2-tert-butyldimethylsilyloxy-2-[3-methyl-2-oxo-5-phenyl-(4S,5R)-1,4-oxazolan-4-yl]-acetaldehyde

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Technology Process of 2-tert-butyldimethylsilyloxy-2-[3-methyl-2-oxo-5-phenyl-(4S,5R)-1,4-oxazolan-4-yl]-acetaldehyde

There total 6 articles about 2-tert-butyldimethylsilyloxy-2-[3-methyl-2-oxo-5-phenyl-(4S,5R)-1,4-oxazolan-4-yl]-acetaldehyde 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: 70.0%

: 651358-97-3
4-[1-tert-butyldimethylsilyloxy-2-(4-methylphenylsulfinyl)-(1R,2Ss)-ethyl]-3-methyl-5-phenyl-(4S,5R)-1,3-oxazolan-2-one

: 651359-04-5
2-tert-butyldimethylsilyloxy-2-[3-methyl-2-oxo-5-phenyl-(4S,5R)-1,4-oxazolan-4-yl]-acetaldehyde

Guidance literature:: 4-[1-tert-butyldimethylsilyloxy-2-(4-methylphenylsulfinyl)-(1R,2Ss)-ethyl]-3-methyl-5-phenyl-(4S,5R)-1,3-oxazolan-2-one; With triethylamine; trifluoroacetic anhydride; In acetonitrile; at 0 ℃; for 0.25h;

With water; sodium hydrogencarbonate; In acetonitrile; for 0.5h;
DOI:10.1016/j.tet.2003.10.032

Reference yield:

: 95482-80-7
1-(4-methylphenylsulfinyl)-4-phenyl-(2R,3E)-3-buten-2-ol

: 651359-04-5
2-tert-butyldimethylsilyloxy-2-[3-methyl-2-oxo-5-phenyl-(4S,5R)-1,4-oxazolan-4-yl]-acetaldehyde

Guidance literature:: Multi-step reaction with 5 steps

1.1: 90 percent / imidazole / CH₂Cl₂ / 1 h / 20 °C

2.1: 80 percent / N-bromosuccinimide; water / toluene / 1 h / 20 °C

3.1: 85 percent / triethylamine / CH₂Cl₂ / 8 h / 20 °C

4.1: 70 percent / NaHMDS / tetrahydrofuran / 1 h / 0 °C

5.1: trifluoroacetic anhydride; triethylamine / acetonitrile / 0.25 h / 0 °C

5.2: 70 percent / NaHCO₃; water / acetonitrile / 0.5 h

With 1H-imidazole; N-Bromosuccinimide; water; sodium hexamethyldisilazane; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; toluene; acetonitrile; 5.1: Pummerer reaction;
DOI:10.1016/j.tet.2003.10.032

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 651359-04-5
2-tert-butyldimethylsilyloxy-2-[3-methyl-2-oxo-5-phenyl-(4S,5R)-1,4-oxazolan-4-yl]-acetaldehyde

Guidance literature:: Multi-step reaction with 5 steps

1.1: 90 percent / imidazole / CH₂Cl₂ / 1 h / 20 °C

2.1: 80 percent / N-bromosuccinimide; water / toluene / 1 h / 20 °C

3.1: 85 percent / triethylamine / CH₂Cl₂ / 8 h / 20 °C

4.1: 70 percent / NaHMDS / tetrahydrofuran / 1 h / 0 °C

5.1: trifluoroacetic anhydride; triethylamine / acetonitrile / 0.25 h / 0 °C

5.2: 70 percent / NaHCO₃; water / acetonitrile / 0.5 h

With 1H-imidazole; N-Bromosuccinimide; water; sodium hexamethyldisilazane; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; toluene; acetonitrile; 5.1: Pummerer reaction;
DOI:10.1016/j.tet.2003.10.032