(R)-4-[N-benzyl(4-methylbenzene)sulfonamido]but-3-yn-2-yl-2-[(tert-butoxycarbonyl)amino]acetate

Base Information

• Chemical Name: (R)-4-[N-benzyl(4-methylbenzene)sulfonamido]but-3-yn-2-yl-2-[(tert-butoxycarbonyl)amino]acetate
• CAS No.: 1427321-65-0
• Molecular Formula: C₂₅H₃₀N₂O₆S
• Molecular Weight: 486.589
• Mol file: 1427321-65-0.mol

Synonyms:(R)-4-[N-benzyl(4-methylbenzene)sulfonamido]but-3-yn-2-yl-2-[(tert-butoxycarbonyl)amino]acetate

Chemical Property of (R)-4-[N-benzyl(4-methylbenzene)sulfonamido]but-3-yn-2-yl-2-[(tert-butoxycarbonyl)amino]acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-[N-benzyl(4-methylbenzene)sulfonamido]but-3-yn-2-yl-2-[(tert-butoxycarbonyl)amino]acetate

There total 2 articles about (R)-4-[N-benzyl(4-methylbenzene)sulfonamido]but-3-yn-2-yl-2-[(tert-butoxycarbonyl)amino]acetate 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: 90.0%

BOC-glycine (4530-20-5) + (R)-N-benzyl-N-(3-hydroxybut-1-yn-1-yl)-4-methylbenzenesulfonamide (1300116-93-1) → (R)-4-[N-benzyl(4-methylbenzene)sulfonamido]but-3-yn-2-yl-2-[(tert-butoxycarbonyl)amino]acetate (1427321-65-0)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20 ℃; for 1.83333h; diastereoselective reaction;

DOI:10.1021/ol400402n

Reference yield:

N-benzyl-p-toluenesulfonamide (1576-37-0) → (R)-4-[N-benzyl(4-methylbenzene)sulfonamido]but-3-yn-2-yl-2-[(tert-butoxycarbonyl)amino]acetate (1427321-65-0)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium phosphate; copper(ll) sulfate pentahydrate; 1,10-Phenanthroline / toluene / 3 h / 80 °C

2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 1.83 h / 0 - 20 °C

With dmap; potassium phosphate; 1,10-Phenanthroline; copper(ll) sulfate pentahydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; toluene;

DOI:10.1021/ol400402n

Reference yield:

(R)-4-[N-benzyl(4-methylbenzene)sulfonamido]but-3-yn-2-yl-2-[(tert-butoxycarbonyl)amino]acetate (1427321-65-0) → C25H30N2O6S

Guidance literature:

(R)-4-[N-benzyl(4-methylbenzene)sulfonamido]but-3-yn-2-yl-2-[(tert-butoxycarbonyl)amino]acetate; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃;

With zinc(II) chloride; In tetrahydrofuran; at -78 ℃; for 2h;

DOI:10.1021/ol400402n

upstream raw materials:

BOC-glycine

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

N-benzyl-p-toluenesulfonamide

Downstream raw materials:

1-tert-butyl 2-methyl (2R,5R)-3-[N-benzyl(4-methylbenzene)sulfonamido]-5-methyl-2,5-dihydro-1H-pyrrole-1,2-dicarboxylate