(-)-(5R,6S,S_S)-1-benzyl-6-[(t-butyldimethylsilyloxy)methyl]-5-(1-naphthyl)-4-(p-tolylsulfinyl)piperazin-2-one

Base Information

• Chemical Name: (-)-(5R,6S,S_S)-1-benzyl-6-[(t-butyldimethylsilyloxy)methyl]-5-(1-naphthyl)-4-(p-tolylsulfinyl)piperazin-2-one
• CAS No.: 878556-96-8
• Molecular Formula: C₃₅H₄₂N₂O₃SSi
• Molecular Weight: 598.882

Synonyms:(-)-(5R,6S,S_S)-1-benzyl-6-[(t-butyldimethylsilyloxy)methyl]-5-(1-naphthyl)-4-(p-tolylsulfinyl)piperazin-2-one

Chemical Property of (-)-(5R,6S,S_S)-1-benzyl-6-[(t-butyldimethylsilyloxy)methyl]-5-(1-naphthyl)-4-(p-tolylsulfinyl)piperazin-2-one

Chemical Property:

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Technology Process of (-)-(5R,6S,S_S)-1-benzyl-6-[(t-butyldimethylsilyloxy)methyl]-5-(1-naphthyl)-4-(p-tolylsulfinyl)piperazin-2-one

There total 5 articles about (-)-(5R,6S,S_S)-1-benzyl-6-[(t-butyldimethylsilyloxy)methyl]-5-(1-naphthyl)-4-(p-tolylsulfinyl)piperazin-2-one 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: 74.0%

(+)-N-benzyl-N-[(1S,2R,SS)-1-(t-butyldimethylsilyloxymethyl)-2-(1-naphthyl)-2-(p-tolylsulfinylamino)ethyl]-2-chloroacetamide → (-)-(5R,6S,SS)-1-benzyl-6-[(t-butyldimethylsilyloxy)methyl]-5-(1-naphthyl)-4-(p-tolylsulfinyl)piperazin-2-one (878556-96-8)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 65 ℃; for 4.5h;

DOI:10.1021/jo052077h

Reference yield:

(-)-(2S,3R,SS)-2-(benzylamino)-3-(1-naphthyl)-3-(p-tolylsulfinylamino)propan-1-ol (878556-85-5) → (-)-(5R,6S,SS)-1-benzyl-6-[(t-butyldimethylsilyloxy)methyl]-5-(1-naphthyl)-4-(p-tolylsulfinyl)piperazin-2-one (878556-96-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 78 percent / imidazole; DMAP / CH₂Cl₂ / 3 h / 20 °C

2: 90 percent / aq. NaHCO₃ / ethyl acetate / 6 h / 0 - 20 °C

3: 74 percent / Cs₂CO₃ / dimethylformamide / 4.5 h / 65 °C

With 1H-imidazole; dmap; sodium hydrogencarbonate; caesium carbonate; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo052077h

Reference yield:

(-)-(1R,2S,SS)-N-[2-benzylamino-3-(t-butyldimethylsilyloxy)-1-(1-naphthyl)prop-1-yl]-p-tolylsulfinamide (878556-89-9) → (-)-(5R,6S,SS)-1-benzyl-6-[(t-butyldimethylsilyloxy)methyl]-5-(1-naphthyl)-4-(p-tolylsulfinyl)piperazin-2-one (878556-96-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / aq. NaHCO₃ / ethyl acetate / 6 h / 0 - 20 °C

2: 74 percent / Cs₂CO₃ / dimethylformamide / 4.5 h / 65 °C

With sodium hydrogencarbonate; caesium carbonate; In ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo052077h

upstream raw materials:

(-)-(2S,3R,S_S)-2-(benzylamino)-3-(1-naphthyl)-3-(p-tolylsulfinylamino)propan-1-ol

(-)-(1R,2S,S_S)-N-[2-benzylamino-3-(t-butyldimethylsilyloxy)-1-(1-naphthyl)prop-1-yl]-p-tolylsulfinamide

tert-butyldimethylsilyl chloride

methyl [(2S,4S,5R,S_S)-5-(1-naphthyl)-2-phenyl-1-(p-tolylsulfinyl)-1,3-imidazolidin-4-yl]carboxylate

Downstream raw materials:

(+)-(5R,6S)-1-benzyl-6-(t-butyldimethylsilyloxymethyl)-5-(1-naphthyl)-5,6-dihydro-1H-pyrazin-2-one

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