N-benzyl-N-[(1R,2R)-2-hydroxy-3-oxo-1-((E)-3-hydroxyprop-1-enyl)butyl]-4-methylbenzenesulfonamide

Base Information

Chemical Name:N-benzyl-N-[(1R,2R)-2-hydroxy-3-oxo-1-((E)-3-hydroxyprop-1-enyl)butyl]-4-methylbenzenesulfonamide
CAS No.:1300117-61-6
Molecular Formula:C₂₁H₂₅NO₅S
Molecular Weight:403.499
Hs Code.:

Synonyms:N-benzyl-N-[(1R,2R)-2-hydroxy-3-oxo-1-((E)-3-hydroxyprop-1-enyl)butyl]-4-methylbenzenesulfonamide

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Chemical Property of N-benzyl-N-[(1R,2R)-2-hydroxy-3-oxo-1-((E)-3-hydroxyprop-1-enyl)butyl]-4-methylbenzenesulfonamide

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Technology Process of N-benzyl-N-[(1R,2R)-2-hydroxy-3-oxo-1-((E)-3-hydroxyprop-1-enyl)butyl]-4-methylbenzenesulfonamide

There total 7 articles about N-benzyl-N-[(1R,2R)-2-hydroxy-3-oxo-1-((E)-3-hydroxyprop-1-enyl)butyl]-4-methylbenzenesulfonamide 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: 84.0%

: 1029537-52-7
N-benzyl-N-{(1R,2R)-2-hydroxy-3-oxo-1-[(E)-3-(4-methoxybenzyloxy)prop-1-ene]butyl}-4-methylbenzenesulfonamide

: 1300117-61-6
N-benzyl-N-[(1R,2R)-2-hydroxy-3-oxo-1-((E)-3-hydroxyprop-1-enyl)butyl]-4-methylbenzenesulfonamide

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 20 ℃; for 2h;
DOI:10.1002/chem.201003265

Reference yield:

: 1029537-47-0
N-benzyl-N-{(3R)-(E)-3-(prop-2-ynyl)oxy-4-[(4-methoxybenzyl)oxy]but-1-enyl}-4-methylbenzenesulfonamide

: 1300117-61-6
N-benzyl-N-[(1R,2R)-2-hydroxy-3-oxo-1-((E)-3-hydroxyprop-1-enyl)butyl]-4-methylbenzenesulfonamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C

1.2: -78 - 20 °C

2.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.17 h / -78 °C

3.1: sulfuric acid; mercury(II) sulfate / tetrahydrofuran; water / 24 h / 20 °C

4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 2 h / 20 °C

With n-butyllithium; sulfuric acid; mercury(II) sulfate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; water; 2.1: Wittig rearrangement;
DOI:10.1002/chem.201003265

Reference yield:

: 1300116-94-2
N-benzyl-N-[(3S)-3-hydroxy-4-(4-methoxybenzyloxy)but-1-ynyl]-4-methylbenzenesulfonamide

: 1300117-61-6
N-benzyl-N-[(1R,2R)-2-hydroxy-3-oxo-1-((E)-3-hydroxyprop-1-enyl)butyl]-4-methylbenzenesulfonamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 0.25 h / 20 °C

2.1: tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide / water; toluene / 0.5 h / 20 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C

3.2: -78 - 20 °C

4.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.17 h / -78 °C

5.1: sulfuric acid; mercury(II) sulfate / tetrahydrofuran; water / 24 h / 20 °C

6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 2 h / 20 °C

With n-butyllithium; sulfuric acid; tetra(n-butyl)ammonium hydrogensulfate; mercury(II) sulfate; sodium bis(2-methoxyethoxy)aluminium dihydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; water; toluene; 4.1: Wittig rearrangement;
DOI:10.1002/chem.201003265