(2R,3R,αR)-tert-butyl 3-(N-benzyl-N-α-methylbenzyl)amino-2-hydroxy-4-phenylbutanoate

Base Information

• Chemical Name: (2R,3R,αR)-tert-butyl 3-(N-benzyl-N-α-methylbenzyl)amino-2-hydroxy-4-phenylbutanoate
• CAS No.: 154568-45-3
• Molecular Formula: C₂₉H₃₅NO₃
• Molecular Weight: 445.602
• Mol file: 154568-45-3.mol

Synonyms:

Chemical Property of (2R,3R,αR)-tert-butyl 3-(N-benzyl-N-α-methylbenzyl)amino-2-hydroxy-4-phenylbutanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,αR)-tert-butyl 3-(N-benzyl-N-α-methylbenzyl)amino-2-hydroxy-4-phenylbutanoate

There total 2 articles about (2R,3R,αR)-tert-butyl 3-(N-benzyl-N-α-methylbenzyl)amino-2-hydroxy-4-phenylbutanoate 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:

lithium benzyl-(R)-1-phenylethylamide + 1-(tert-butoxycarbonyl)-2-benzylethene (154457-63-3) → (2R,3R,αR)-tert-butyl 3-(N-benzyl-N-α-methylbenzyl)amino-2-hydroxy-4-phenylbutanoate (154568-45-3)

Guidance literature:

With n-butyllithium; (+)-(2S,8aS)-(camphorylsulfonyl)oxaziridine; acetic acid; lithium diisopropyl amide; Yield given. Multistep reaction; 1.) THF, -78 deg C, 30 min; 3 h; 2.) THF, 0 deg C, 40 min; 3.) THF, -78 deg C, 45 min; 2 h; to 0 deg C 15 min;

DOI:10.1016/S0040-4020(01)89672-1

Reference yield:

lithium benzyl-(R)-1-phenylethylamide + 1-(tert-butoxycarbonyl)-2-benzylethene (154457-63-3) → (2S,3R,αR)-tert-butyl 3-(N-benzyl-N-α-methylbenzyl)amino-2-hydroxy-4-phenylbutanoate + (2R,3R,αR)-tert-butyl 3-(N-benzyl-N-α-methylbenzyl)amino-2-hydroxy-4-phenylbutanoate (154568-45-3)

Guidance literature:

With n-butyllithium; (+)-(2S,8aS)-(camphorylsulfonyl)oxaziridine; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) THF, 2 h; 2.) THF, 1 h, -78 deg C, to 0 deg C 20 min;

DOI:10.1016/S0040-4020(01)89672-1

Reference yield:

(2R,3R,αR)-tert-butyl 3-(N-benzyl-N-α-methylbenzyl)amino-2-hydroxy-4-phenylbutanoate (154568-45-3) → (4R,5R)-5-(tert-butoxycarbonyl)-4-(phenylmethyl)-2-oxazolidinone

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / 10 percent Pd/C / 5320 Torr / Ambient temperature

2: triethylamine, carbonyldiimidazole / CH₂Cl₂

With hydrogen; triethylamine; 1,1'-carbonyldiimidazole; palladium on activated charcoal; In dichloromethane;

DOI:10.1016/S0040-4020(01)89672-1

upstream raw materials:

1-(tert-butoxycarbonyl)-2-benzylethene