(S_S,3R,5R)-(+)-3-hydroxy-5-phenyl-5-N-(p-toluenesulfinyl)aminopentanoic acid N-methoxy-N-methylamide

Base Information

• Chemical Name: (S_S,3R,5R)-(+)-3-hydroxy-5-phenyl-5-N-(p-toluenesulfinyl)aminopentanoic acid N-methoxy-N-methylamide
• CAS No.: 620158-90-9
• Molecular Formula: C₂₀H₂₆N₂O₄S
• Molecular Weight: 390.503

Synonyms:(S_S,3R,5R)-(+)-3-hydroxy-5-phenyl-5-N-(p-toluenesulfinyl)aminopentanoic acid N-methoxy-N-methylamide

Chemical Property of (S_S,3R,5R)-(+)-3-hydroxy-5-phenyl-5-N-(p-toluenesulfinyl)aminopentanoic acid N-methoxy-N-methylamide

Chemical Property:

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Technology Process of (S_S,3R,5R)-(+)-3-hydroxy-5-phenyl-5-N-(p-toluenesulfinyl)aminopentanoic acid N-methoxy-N-methylamide

There total 1 articles about (S_S,3R,5R)-(+)-3-hydroxy-5-phenyl-5-N-(p-toluenesulfinyl)aminopentanoic acid N-methoxy-N-methylamide 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: 90.0%

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + Methyl (SS,3R,5R)-(+)-3-hydroxy-5-phenyl-5-(p-toluenesulfinylamino)pentanoate (326477-46-7) → (SS,3R,5R)-(+)-3-hydroxy-5-phenyl-5-N-(p-toluenesulfinyl)aminopentanoic acid N-methoxy-N-methylamide (620158-90-9)

Guidance literature:

N,O-dimethylhydroxylamine*hydrochloride; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h;

Methyl (S_S,3R,5R)-(+)-3-hydroxy-5-phenyl-5-(p-toluenesulfinylamino)pentanoate; In tetrahydrofuran; hexane; at -78 ℃;

DOI:10.1021/ol035390j

Reference yield: 88.0%

methylmagnesium bromide (75-16-1) + (SS,3R,5R)-(+)-3-hydroxy-5-phenyl-5-N-(p-toluenesulfinyl)aminopentanoic acid N-methoxy-N-methylamide (620158-90-9) → (SS,1R,3R)-(+)-1-phenyl-1-N-(p-toluenesulfinyl)amino-3-hydroxy-5-oxo-hexane (620158-91-0)

Guidance literature:

In diethyl ether; at -78 - 20 ℃;

DOI:10.1021/ol035390j

Reference yield:

(SS,3R,5R)-(+)-3-hydroxy-5-phenyl-5-N-(p-toluenesulfinyl)aminopentanoic acid N-methoxy-N-methylamide (620158-90-9) → (2R,4S,6R)-4-hydroxy-6-methyl-2-phenylpiperidine

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / diethyl ether / -78 - 20 °C

2: aq. HCl / tetrahydrofuran / 0.25 h / 0 °C

3: 70 percent / DIBAL-H-n-BuLi "ate" complex / tetrahydrofuran; diethyl ether; hexane / -78 - 0 °C

With hydrogenchloride; n-butyllithium; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; hexane;

DOI:10.1021/ol035390j

upstream raw materials:

N,O-dimethylhydroxylamine*hydrochloride

Methyl (S_S,3R,5R)-(+)-3-hydroxy-5-phenyl-5-(p-toluenesulfinylamino)pentanoate

Downstream raw materials:

(S_S,1R,3R)-(+)-1-phenyl-1-N-(p-toluenesulfinyl)amino-3-hydroxy-5-oxo-hexane

(2R,4R)-6-Methyl-2-phenyl-2,3,4,5-tetrahydro-pyridin-4-ol

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