Methyl (R_S,3R,5S)-(-)-3-hydroxy-5-phenyl-5-(p-toluenesulfinylamino)pentanoate

Base Information

• Chemical Name: Methyl (R_S,3R,5S)-(-)-3-hydroxy-5-phenyl-5-(p-toluenesulfinylamino)pentanoate
• CAS No.: 326477-53-6
• Molecular Formula: C₁₉H₂₃NO₄S
• Molecular Weight: 361.462
• Mol file: 326477-53-6.mol

Synonyms:Methyl (R_S,3R,5S)-(-)-3-hydroxy-5-phenyl-5-(p-toluenesulfinylamino)pentanoate

Chemical Property of Methyl (R_S,3R,5S)-(-)-3-hydroxy-5-phenyl-5-(p-toluenesulfinylamino)pentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl (R_S,3R,5S)-(-)-3-hydroxy-5-phenyl-5-(p-toluenesulfinylamino)pentanoate

There total 3 articles about Methyl (R_S,3R,5S)-(-)-3-hydroxy-5-phenyl-5-(p-toluenesulfinylamino)pentanoate 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: 72.0%

Methyl (RS,S)-(-)-3-oxo-5-phenyl-5-(p-toluenesulfinylamino)pentanoate (326477-52-5) → Methyl (RS,3R,5S)-(-)-3-hydroxy-5-phenyl-5-(p-toluenesulfinylamino)pentanoate (326477-53-6)

Guidance literature:

With zinc(II) tetrahydroborate; In tetrahydrofuran; diethyl ether; at -78 ℃; for 5h;

DOI:10.1055/s-2000-8710

Reference yield: 44.0%

Methyl (RS,S)-(-)-3-oxo-5-phenyl-5-(p-toluenesulfinylamino)pentanoate (326477-52-5) → Methyl (RS,3S,5S)-(+)-3-hydroxy-5-phenyl-5-(p-toluenesulfinylamino)pentanoate + Methyl (RS,3R,5S)-(-)-3-hydroxy-5-phenyl-5-(p-toluenesulfinylamino)pentanoate (326477-53-6)

Guidance literature:

With lithium triethylborohydride; In diethyl ether; at -78 ℃; for 5h;

DOI:10.1055/s-2000-8710

Reference yield:

(R,E)-N-benzylidene-4-methylbenzenesulfinamide (158109-78-5) → Methyl (RS,3R,5S)-(-)-3-hydroxy-5-phenyl-5-(p-toluenesulfinylamino)pentanoate (326477-53-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / NaHMDS / tetrahydrofuran; diethyl ether / 6 h / -78 - -42 °C

2: LiEt₃BH / diethyl ether / 5 h / -78 °C

With sodium hexamethyldisilazane; lithium triethylborohydride; In tetrahydrofuran; diethyl ether;

DOI:10.1055/s-2000-8710

upstream raw materials:

Methyl (R_S,S)-(-)-3-oxo-5-phenyl-5-(p-toluenesulfinylamino)pentanoate

(R,E)-N-benzylidene-4-methylbenzenesulfinamide

Downstream raw materials:

(4R,6S)-(-)-4-Hydroxy-6-phenylpiperidin-2-one

(2S,4S)-(-)-4-Acetoxy-2-phenyl-1-trifluoroacetylpiperidine

(2S,4S)-(-)-2-Phenylpiperidine-4-ol