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

Base Information

• Chemical Name: (S_S,3S,5R)-(+)-methyl 3-hydroxy-5-(p-toluenesulfinylamino)-5-phenyl-pentanoate
• CAS No.: 326477-45-6
• Molecular Formula: C₁₉H₂₃NO₄S
• Molecular Weight: 361.462

Synonyms:(S_S,3S,5R)-(+)-methyl 3-hydroxy-5-(p-toluenesulfinylamino)-5-phenyl-pentanoate

Chemical Property of (S_S,3S,5R)-(+)-methyl 3-hydroxy-5-(p-toluenesulfinylamino)-5-phenyl-pentanoate

Chemical Property:

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Technology Process of (S_S,3S,5R)-(+)-methyl 3-hydroxy-5-(p-toluenesulfinylamino)-5-phenyl-pentanoate

There total 1 articles about (S_S,3S,5R)-(+)-methyl 3-hydroxy-5-(p-toluenesulfinylamino)-5-phenyl-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: 69.0%

methyl (SS,R)-(+)-methyl 3-oxo-5-phenyl-5-(p-toluenesulfinylamino)pentanoate (267011-72-3) → (SS,3S,5R)-(+)-methyl 3-hydroxy-5-(p-toluenesulfinylamino)-5-phenyl-pentanoate (326477-45-6) + Methyl (SS,3R,5R)-(+)-3-hydroxy-5-phenyl-5-(p-toluenesulfinylamino)pentanoate (326477-46-7)

Guidance literature:

With zinc(II) tetrahydroborate; In tetrahydrofuran; diethyl ether; at -78 ℃; for 5h; Further Variations:; Reagents; Solvents; Temperatures; Times; Product distribution;

DOI:10.1055/s-2000-8710

Reference yield: 98.0%

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + (SS,3S,5R)-(+)-methyl 3-hydroxy-5-(p-toluenesulfinylamino)-5-phenyl-pentanoate (326477-45-6) → (SS,3S,5R)-(+)-3-hydroxy-5-phenyl-5-N-(p-toluenesulfinyl)aminopentanoic acid N-methoxy-N-methylamide (620158-82-9)

Guidance literature:

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

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

DOI:10.1021/ol035390j

Reference yield: 97.0%

(SS,3S,5R)-(+)-methyl 3-hydroxy-5-(p-toluenesulfinylamino)-5-phenyl-pentanoate (326477-45-6) → (4S,6R)-(+)-4-Hydroxy-6-phenylpiperidin-2-one (326477-44-5)

Guidance literature:

(S_S,3S,5R)-(+)-methyl 3-hydroxy-5-(p-toluenesulfinylamino)-5-phenyl-pentanoate; With trifluoroacetic acid; In methanol; at 20 ℃; for 1h;

With sodium hydrogencarbonate; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1055/s-2000-8710

upstream raw materials:

methyl (S_S,R)-(+)-methyl 3-oxo-5-phenyl-5-(p-toluenesulfinylamino)pentanoate

Downstream raw materials:

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

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

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

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

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