methyl (2S,3S)-3-[benzyl(4-methylbenzenesulfonyl)amino]-2-hydroxy-pent-4-enoate

Base Information

Chemical Name:methyl (2S,3S)-3-[benzyl(4-methylbenzenesulfonyl)amino]-2-hydroxy-pent-4-enoate
CAS No.:1300117-24-1
Molecular Formula:C₂₀H₂₃NO₅S
Molecular Weight:389.472
Hs Code.:

Synonyms:

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Chemical Property of methyl (2S,3S)-3-[benzyl(4-methylbenzenesulfonyl)amino]-2-hydroxy-pent-4-enoate

Chemical Property:

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Technology Process of methyl (2S,3S)-3-[benzyl(4-methylbenzenesulfonyl)amino]-2-hydroxy-pent-4-enoate

There total 5 articles about methyl (2S,3S)-3-[benzyl(4-methylbenzenesulfonyl)amino]-2-hydroxy-pent-4-enoate 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:

: 1576-37-0
N-benzyl-p-toluenesulfonamide

: 1300117-24-1
methyl (2S,3S)-3-[benzyl(4-methylbenzenesulfonyl)amino]-2-hydroxy-pent-4-enoate

Guidance literature:: Multi-step reaction with 5 steps

1: 4-methyl-morpholine / acetonitrile / 2 h / 0 °C

2: diisobutylaluminium hydride / hexane; dichloromethane / 0.33 h / -78 °C

3: tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide / water; toluene / 2 h / 20 °C

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

5: hydrogenchloride / 5 h / Reflux

With 4-methyl-morpholine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; tetra(n-butyl)ammonium hydrogensulfate; diisobutylaluminium hydride; sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; water; toluene; acetonitrile; 4: Wittig rearrangement;
DOI:10.1002/chem.201003265

Reference yield:

: N-benzyl-N-(3-hydroxyprop-1-yn-1-yl)-4-methylbenzenesulfonamide

: 1300117-24-1
methyl (2S,3S)-3-[benzyl(4-methylbenzenesulfonyl)amino]-2-hydroxy-pent-4-enoate

Guidance literature:: Multi-step reaction with 4 steps

1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran / 20 °C

2: tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide / water; toluene / 2 h / 20 °C

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

4: hydrogenchloride / 5 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: Wittig rearrangement;
DOI:10.1002/chem.201003265

Reference yield:

: 950777-54-5
(E)-N-benzyl-N-(3-hydroxyprop-1-en-1-yl)-4-methylbenzenesulfonamide

: 1300117-24-1
methyl (2S,3S)-3-[benzyl(4-methylbenzenesulfonyl)amino]-2-hydroxy-pent-4-enoate

Guidance literature:: Multi-step reaction with 3 steps

1: tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide / water; toluene / 2 h / 20 °C

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

3: hydrogenchloride / 5 h / Reflux

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; water; toluene; 2: Wittig rearrangement;
DOI:10.1002/chem.201003265