[2S,4R]-(-)-methyl 2-methyl-5-phenyl-4-(p-toluenesulfonylamino)pentanoate

Base Information

• Chemical Name: [2S,4R]-(-)-methyl 2-methyl-5-phenyl-4-(p-toluenesulfonylamino)pentanoate
• CAS No.: 362496-00-2
• Molecular Formula: C₂₀H₂₅NO₄S
• Molecular Weight: 375.489

Synonyms:[2S,4R]-(-)-methyl 2-methyl-5-phenyl-4-(p-toluenesulfonylamino)pentanoate

Chemical Property of [2S,4R]-(-)-methyl 2-methyl-5-phenyl-4-(p-toluenesulfonylamino)pentanoate

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Technology Process of [2S,4R]-(-)-methyl 2-methyl-5-phenyl-4-(p-toluenesulfonylamino)pentanoate

There total 2 articles about [2S,4R]-(-)-methyl 2-methyl-5-phenyl-4-(p-toluenesulfonylamino)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:

[2S,4R,1'S,2'S]-(+)-N,2-dimethyl-5-phenyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)-4-(p-toluenesulfonylamino)pentanamide (362495-79-2) → [2S,4R]-(-)-methyl 2-methyl-5-phenyl-4-(p-toluenesulfonylamino)pentanoate (362496-00-2)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂SO₄ / dioxane / 5 h / Heating

2: 85 percent / HCl / 16 h / Heating

With hydrogenchloride; sulfuric acid; In 1,4-dioxane;

DOI:10.1002/anie.200601259

Reference yield:

(S)-(+)-2-benzyl-1-(p-tolylsulfonyl)aziridine (71535-50-7,77210-52-7,62596-64-9) → [2S,4R]-(-)-methyl 2-methyl-5-phenyl-4-(p-toluenesulfonylamino)pentanoate (362496-00-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / lithium diisopropylamide; LiCl / tetrahydrofuran

2: 87 percent / aq. H₂SO₄ / dioxane / Heating

3: 91 percent / conc. HCl / Heating

With hydrogenchloride; sulfuric acid; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1021/jo0103571

Reference yield: 76.0%

[2S,4R]-(-)-methyl 2-methyl-5-phenyl-4-(p-toluenesulfonylamino)pentanoate (362496-00-2) → [3S,5R]-(+)-5-benzyl-3-methyl-1-(p-toluenesulfonyl)pyrrolidin-2-one

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -20 ℃;

DOI:10.1021/jo0103571

upstream raw materials:

[2S,4R,1'S,2'S]-(+)-N,2-dimethyl-5-phenyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)-4-(p-toluenesulfonylamino)pentanamide

(S)-(+)-2-benzyl-1-(p-tolylsulfonyl)aziridine

Downstream raw materials:

methyl (2S,4R)-4-[(tert-butoxycarbonyl)amino]-2-methyl-5-phenylpentanoate

methyl (2S,4R)-4-{[(2-{(1R,3R)-3-[(tert-butoxycarbonyl)amino]-1-hydroxy-4-methylpentyl}-1,3-thiazol-4-yl)carbonyl]amino}-2-methyl-5-phenylpentanoate

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