(E)-(2S,3S)-3-[benzyl(4-methylbenzenesulfonyl)amino]-2-hydroxy-hex-4-enoic acid methyl ester

Base Information

• Chemical Name: (E)-(2S,3S)-3-[benzyl(4-methylbenzenesulfonyl)amino]-2-hydroxy-hex-4-enoic acid methyl ester
• CAS No.: 1300117-30-9
• Molecular Formula: C₂₁H₂₅NO₅S
• Molecular Weight: 403.499
• Mol file: 1300117-30-9.mol

Synonyms:

Chemical Property of (E)-(2S,3S)-3-[benzyl(4-methylbenzenesulfonyl)amino]-2-hydroxy-hex-4-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(2S,3S)-3-[benzyl(4-methylbenzenesulfonyl)amino]-2-hydroxy-hex-4-enoic acid methyl ester

There total 4 articles about (E)-(2S,3S)-3-[benzyl(4-methylbenzenesulfonyl)amino]-2-hydroxy-hex-4-enoic acid methyl ester 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:

N-benzyl-N-{(E)-(3R)-[2-((3aR,8aS)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]-oxazol-3-yl)-2-oxoethoxy]but-1-enyl}-4-methylbenzenesulfonamide (1300117-26-3) → (E)-(2S,3S)-3-[benzyl(4-methylbenzenesulfonyl)amino]-2-hydroxy-hex-4-enoic acid methyl ester (1300117-30-9)

Guidance literature:

Multi-step reaction with 2 steps

1: N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C

2: hydrogenchloride / 3 h / Reflux

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane; In tetrahydrofuran; 1: Wittig rearrangement;

DOI:10.1002/chem.201003265

Reference yield:

(R)-N-benzyl-N-(3-hydroxybut-1-yn-1-yl)-4-methylbenzenesulfonamide (1300116-93-1) → (E)-(2S,3S)-3-[benzyl(4-methylbenzenesulfonyl)amino]-2-hydroxy-hex-4-enoic acid methyl ester (1300117-30-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 0.5 h / 20 °C

2.1: tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide / water; toluene / 3 h / 20 °C

2.2: 0.5 h / 20 °C

3.1: N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C

4.1: hydrogenchloride / 3 h / Reflux

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; tetra(n-butyl)ammonium hydrogensulfate; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; water; toluene; 3.1: Wittig rearrangement;

DOI:10.1002/chem.201003265

Reference yield:

N-benzyl-N-[(3R)-3-(tert-butyldiphenylsilyloxy)but-1-ynyl]-4-methylbenzenesulfonamide (1300116-89-5) → (E)-(2S,3S)-3-[benzyl(4-methylbenzenesulfonyl)amino]-2-hydroxy-hex-4-enoic acid methyl ester (1300117-30-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C

2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 0.5 h / 20 °C

3.1: tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide / water; toluene / 3 h / 20 °C

3.2: 0.5 h / 20 °C

4.1: N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C

5.1: hydrogenchloride / 3 h / Reflux

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydrogensulfate; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; water; toluene; 4.1: Wittig rearrangement;

DOI:10.1002/chem.201003265

upstream raw materials:

N-benzyl-N-{(E)-(3R)-[2-((3aR,8aS)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]-oxazol-3-yl)-2-oxoethoxy]but-1-enyl}-4-methylbenzenesulfonamide

(R)-N-benzyl-N-(3-hydroxybut-1-yn-1-yl)-4-methylbenzenesulfonamide

N-benzyl-N-[(3R)-3-(tert-butyldiphenylsilyloxy)but-1-ynyl]-4-methylbenzenesulfonamide

N-benzyl-N-((E)-(3R)-3-hydroxybut-1-enyl)-4-methylbenzenesulfonamide