(5S,S_R)-5-[2-(N,N-dimethylamino)phenylsulfinyl]-2-(triisopropylsilyloxy)methyl-2-cyclopentenone

Base Information

• Chemical Name: (5S,S_R)-5-[2-(N,N-dimethylamino)phenylsulfinyl]-2-(triisopropylsilyloxy)methyl-2-cyclopentenone
• CAS No.: 642473-03-8
• Molecular Formula: C₂₃H₃₇NO₃SSi
• Molecular Weight: 435.703
• Mol file: 642473-03-8.mol

Synonyms:(5S,S_R)-5-[2-(N,N-dimethylamino)phenylsulfinyl]-2-(triisopropylsilyloxy)methyl-2-cyclopentenone

Chemical Property of (5S,S_R)-5-[2-(N,N-dimethylamino)phenylsulfinyl]-2-(triisopropylsilyloxy)methyl-2-cyclopentenone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,S_R)-5-[2-(N,N-dimethylamino)phenylsulfinyl]-2-(triisopropylsilyloxy)methyl-2-cyclopentenone

There total 5 articles about (5S,S_R)-5-[2-(N,N-dimethylamino)phenylsulfinyl]-2-(triisopropylsilyloxy)methyl-2-cyclopentenone 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: 53.0%

3-(triisopropylsilyloxy)propyne (145383-93-3) + (R)-2-(N,N-dimethylamino)phenyl vinyl sulfoxide (642472-93-3) → (5R,SR)-5-[2-(N,N-dimethylamino)phenylsulfinyl]-2-(triisopropylsilyloxy)methyl-2-cyclopentenone + (5S,SR)-5-[2-(N,N-dimethylamino)phenylsulfinyl]-2-(triisopropylsilyloxy)methyl-2-cyclopentenone (642473-03-8)

Guidance literature:

3-(triisopropylsilyloxy)propyne; Co₂(CO)8; In acetonitrile; at 20 ℃; for 1h;

(R)-2-(N,N-dimethylamino)phenyl vinyl sulfoxide; With 4-methylmorpholine N-oxide; In acetonitrile; at 0 ℃; for 2h;

DOI:10.1021/ja038491l

Reference yield:

(1R,2S)-2-(p-tolylsulfonylamino)-1-phenylpropyl (S)-2-(N,N-dimethylamino)phenyl sulfinate (642473-02-7) → (5S,SR)-5-[2-(N,N-dimethylamino)phenylsulfinyl]-2-(triisopropylsilyloxy)methyl-2-cyclopentenone (642473-03-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 66 percent / tetrahydrofuran / 2 h / -78 °C

2.2: N-methylmorpholine N-oxide*H₂O / acetonitrile

In tetrahydrofuran; 2.2: intermolecular Pauson-Khand reaction;

DOI:10.1002/chem.200400443

Reference yield:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → (5S,SR)-5-[2-(N,N-dimethylamino)phenylsulfinyl]-2-(triisopropylsilyloxy)methyl-2-cyclopentenone (642473-03-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 24 h / 20 °C

2.2: N-methylmorpholine N-oxide*H₂O / acetonitrile

With 2,6-dimethylpyridine; In dichloromethane; 2.2: intermolecular Pauson-Khand reaction;

DOI:10.1002/chem.200400443

upstream raw materials:

3-(triisopropylsilyloxy)propyne

(R)-2-(N,N-dimethylamino)phenyl vinyl sulfoxide

triisopropylsilyl trifluoromethanesulfonate

(2S,S_S)-1,2-dihydroxypropyl-2-O-[2-(N,N-dimethylamino)phenyl]-1,1-diphenyl sulfinate

Downstream raw materials:

(3S,4S,S_R)-3-(tert-butyldimethylsilyloxy)-4-[2-(N,N-dimethylamino)phenylsulfinyl]-2-(triisopropylsilyloxy)methylcyclopentene

(1S,5S,S_R)-5-[2-(N,N-dimethylamino)phenylsulfinyl]-2-(triisopropylsilyloxy)methyl-2-cyclopenten-1-ol

(-)-pentenomycin