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

Base Information

• Chemical Name: 1-tert-butyldimethylsilyloxy-1-[3-methyl-2-oxo-5-phenyl-(4S,5R)-1,3-oxazolan-4-yl]-methyl-2-oxoundecyl acetate
• CAS No.: 651359-07-8
• Molecular Formula: C₃₀H₄₉NO₆Si
• Molecular Weight: 547.808
• Mol file: 651359-07-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about 1-tert-butyldimethylsilyloxy-1-[3-methyl-2-oxo-5-phenyl-(4S,5R)-1,3-oxazolan-4-yl]-methyl-2-oxoundecyl acetate 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: 90.0%

acetic anhydride (108-24-7) + 2-hydroxy-1-tert-butyldimethylsilyloxy-1-[3-methyl-2-oxo-5-phenyl-(4S,5R)-1,3-oxazolan-4-yl]-(1R)-dodecan-3-one (651359-06-7) → 1-tert-butyldimethylsilyloxy-1-[3-methyl-2-oxo-5-phenyl-(4S,5R)-1,3-oxazolan-4-yl]-methyl-2-oxoundecyl acetate (651359-07-8)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1016/j.tet.2003.10.032

Reference yield:

1-(4-methylphenylsulfinyl)-4-phenyl-(2R,3E)-3-buten-2-ol (95482-80-7) → 1-tert-butyldimethylsilyloxy-1-[3-methyl-2-oxo-5-phenyl-(4S,5R)-1,3-oxazolan-4-yl]-methyl-2-oxoundecyl acetate (651359-07-8)

Guidance literature:

Multi-step reaction with 8 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

6.1: n-butyl lithium / tetrahydrofuran; hexane / 2 h / -23 °C

6.2: 70 percent / tetrahydrofuran; hexane / 0.17 h / -78 °C

7.1: 80 percent / iodosobenzene bis(trifluoroacetate) / acetonitrile; H₂O / 1 h / 0 °C

8.1: 90 percent / triethylamine; DMAP / CH₂Cl₂ / 0.5 h / 20 °C

With 1H-imidazole; dmap; N-Bromosuccinimide; n-butyllithium; water; sodium hexamethyldisilazane; triethylamine; trifluoroacetic anhydride; bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; hexane; dichloromethane; water; toluene; acetonitrile; 5.1: Pummerer reaction;

DOI:10.1016/j.tet.2003.10.032

Reference yield:

2-tert-butyldimethylsilyloxy-2-[3-methyl-2-oxo-5-phenyl-(4S,5R)-1,4-oxazolan-4-yl]-acetaldehyde (651359-04-5) → 1-tert-butyldimethylsilyloxy-1-[3-methyl-2-oxo-5-phenyl-(4S,5R)-1,3-oxazolan-4-yl]-methyl-2-oxoundecyl acetate (651359-07-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-butyl lithium / tetrahydrofuran; hexane / 2 h / -23 °C

1.2: 70 percent / tetrahydrofuran; hexane / 0.17 h / -78 °C

2.1: 80 percent / iodosobenzene bis(trifluoroacetate) / acetonitrile; H₂O / 1 h / 0 °C

3.1: 90 percent / triethylamine; DMAP / CH₂Cl₂ / 0.5 h / 20 °C

With dmap; n-butyllithium; triethylamine; bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; hexane; dichloromethane; water; acetonitrile;

DOI:10.1016/j.tet.2003.10.032

upstream raw materials:

acetic anhydride

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

1-(4-methylphenylsulfinyl)-4-phenyl-(2R,3E)-3-buten-2-ol

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

Downstream raw materials:

(+)-preussin