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

Base Information

• Chemical Name: (-)-(1R,2S,S_S)-N-[2-benzylamino-3-(t-butyldimethylsilyloxy)-1-(1-naphthyl)prop-1-yl]-p-tolylsulfinamide
• CAS No.: 878556-89-9
• Molecular Formula: C₃₃H₄₂N₂O₂SSi
• Molecular Weight: 558.86

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

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

Chemical Property:

Purity/Quality:

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

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

methyl [(2S,4S,5R,SS)-5-(1-naphthyl)-2-phenyl-1-(p-tolylsulfinyl)-1,3-imidazolidin-4-yl]carboxylate (596823-41-5) → (-)-(1R,2S,SS)-N-[2-benzylamino-3-(t-butyldimethylsilyloxy)-1-(1-naphthyl)prop-1-yl]-p-tolylsulfinamide (878556-89-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / LiAlH₄ / diethyl ether / 4 h

2: 78 percent / imidazole; DMAP / CH₂Cl₂ / 3 h / 20 °C

With 1H-imidazole; dmap; lithium aluminium tetrahydride; In diethyl ether; dichloromethane;

DOI:10.1021/jo052077h

Reference yield: 90.0%

(-)-(1R,2S,SS)-N-[2-benzylamino-3-(t-butyldimethylsilyloxy)-1-(1-naphthyl)prop-1-yl]-p-tolylsulfinamide (878556-89-9) + chloroacetyl chloride (79-04-9) → (+)-N-benzyl-N-[(1S,2R,SS)-1-(t-butyldimethylsilyloxymethyl)-2-(1-naphthyl)-2-(p-tolylsulfinylamino)ethyl]-2-chloroacetamide

Guidance literature:

With sodium hydrogencarbonate; In ethyl acetate; at 0 - 20 ℃; for 6h;

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-hydroxymethyl-5-(1-naphthyl)-4-(p-tolylsulfinyl)piperazin-2-one

Guidance literature:

Multi-step reaction with 2 steps

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

2: 87 percent / TBAF / tetrahydrofuran / 4 h / 0 - 20 °C

With tetrabutyl ammonium fluoride; sodium hydrogencarbonate; In tetrahydrofuran; ethyl acetate;

DOI:10.1021/jo052077h

upstream raw materials:

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

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

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