(-)-(2S,3R,S_S)-2-(benzylamino)-5-phenyl-3-(p-tolylsulfinylamino)pentan-1-ol

Base Information

• Chemical Name: (-)-(2S,3R,S_S)-2-(benzylamino)-5-phenyl-3-(p-tolylsulfinylamino)pentan-1-ol
• CAS No.: 467471-30-3
• Molecular Formula: C₂₅H₃₀N₂O₂S
• Molecular Weight: 422.591

Synonyms:(-)-(2S,3R,S_S)-2-(benzylamino)-5-phenyl-3-(p-tolylsulfinylamino)pentan-1-ol

Chemical Property of (-)-(2S,3R,S_S)-2-(benzylamino)-5-phenyl-3-(p-tolylsulfinylamino)pentan-1-ol

Chemical Property:

Purity/Quality:

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Technology Process of (-)-(2S,3R,S_S)-2-(benzylamino)-5-phenyl-3-(p-tolylsulfinylamino)pentan-1-ol

There total 5 articles about (-)-(2S,3R,S_S)-2-(benzylamino)-5-phenyl-3-(p-tolylsulfinylamino)pentan-1-ol 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: 68.0%

(+)-methyl [(2S,4S,5R,SS)-2-phenyl-5-(2-phenylethyl)-1-(p-tolylsulfinyl)-1,3-imidazolidin-4-yl]carboxylate (596823-42-6) → (-)-(2S,3R,SS)-2-(benzylamino)-5-phenyl-3-(p-tolylsulfinylamino)pentan-1-ol (467471-30-3)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 - 20 ℃; for 4.5h;

DOI:10.1002/chem.200204674

Reference yield:

3-phenyl-propionaldehyde (104-53-0) → (-)-(2S,3R,SS)-2-(benzylamino)-5-phenyl-3-(p-tolylsulfinylamino)pentan-1-ol (467471-30-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 85 percent / Ti(OEt)4 / CH₂Cl₂ / 4.5 h / Heating

2.1: LDA / tetrahydrofuran / -78 °C

2.2: BF₃*Et₂O / tetrahydrofuran / 0.17 h / -78 - -20 °C

3.1: 1.075 g / CHCl₃ / 20 °C

4.1: 68 percent / LiAlH₄ / diethyl ether / 4.5 h / 0 - 20 °C

With titanium(IV) tetraethanolate; lithium aluminium tetrahydride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform;

DOI:10.1002/chem.200204674

Reference yield:

C26H28N2O3S → (-)-(2S,3R,SS)-2-(benzylamino)-5-phenyl-3-(p-tolylsulfinylamino)pentan-1-ol (467471-30-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.075 g / CHCl₃ / 20 °C

2: 68 percent / LiAlH₄ / diethyl ether / 4.5 h / 0 - 20 °C

With lithium aluminium tetrahydride; In diethyl ether; chloroform;

DOI:10.1002/chem.200204674

upstream raw materials:

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

3-phenyl-propionaldehyde

(S)-p-toluenesulfinimide

(S)-(+)-N-(3-phenylpropylidene)-p-toluenesulfinamide

Downstream raw materials:

(+)-(5R,6S)-1-benzyl-6-hydroxymethyl-5-(2-phenylethyl)piperazine-2,3-dione

4-Methyl-benzenesulfinic acid [(R)-1-((S)-4-benzyl-5,6-dioxo-morpholin-3-yl)-3-phenyl-propyl]-amide

(+)-N-benzyl-N-[(1S,2R,S_S)-1-(t-butyldimethylsilyloxymethyl)-4-phenyl-2-(p-tolylsulfinylamino)but-1-yl]-2-chloroacetamide

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

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